卟啉酞菁化合物的设计、合成、性质及可控的自组装纳米结构研究
|
摘要
卟啉酞菁化合物以及三明治型稀土卟啉酞菁配合物作为新型的功能材料,由于其具有迷人的、独特的光学、电学、磁性以及其它的与其分子内部大环之间π-π相互作用有关的物理性质,因此使得它们在分子电子学、分子信息存储和非线性光学上具有潜在的应用价值,在材料科学领域拥有广阔的应用前景。近年来,该类配合物的有序超分子聚集体和纳米尺度组装研究已经成为了热点领域。但是,对化学家和材料学家来说,通过模拟和设计分子的结构调节分子间作用力以获得所希望得到有机纳米结构材料的形貌仍然是一个挑战。本论文主要设计、合成了具有特定分子结构和特殊性质的新型卟啉和酞菁大环配合物;通过自组装方法,将上述合成的目标化合物组装成各种高级有序的聚集体材料,探讨组装过程的机理和动力学过程,研究分子结构对分子在聚集体中排列方式的影响以及聚集体结构和性质之间的关系,总结变化规律,系统的研究总结各种具有更高性能的新型分子功能材料的思路和方法。其内容主要包括以下几个部分:
1、两亲性卟啉配合物自组装纳米结构的研究
有机功能分子自组装得到的有序纳米结构被预期在纳米科学与纳米技术中获得广泛的应用。自组装过程是一种自发的过程,是指分子间通过非共价键例如,氢键、配位键、堆积效应、静电相互作用、亲/疏水相互作用等形成的结构稳定、复杂有序且具有某种特定功能的纳米聚集体或超分子结构的过程。近十年来,通过分子的相互作用进行有机分子纳米结构自组装的研究一直是广大科研工作者研究的热点。各种各样形貌的有机纳米结构的报道层出不穷:纳米线、纳米棒、纳米颗粒和纳米管等等。然而,对化学家和材料学家来说,通过模拟和设计分子的结构调节分子间作用力以获得所希望的有机纳米结构材料的形貌仍然是一个挑战。在本章中,我们设计了三种卟啉分子Metal free tetrakis(4-hydroxyphenyl)porphyrin H_2THPP(1),Tetrakis(4-hydroxyphenyl)porphyrinato copper complex CuTHPP(2),和Metal freetetraphenylporphyrin H_2TPP(3)。利用相转移方法,把它们组装成有机纳米聚集体。参考化合物3利用紫外(UV)、红外(FT-IR)、透射电镜(TEM)、扫描电镜(SEM)、原子力显微镜(AFM)等表征手段系统研究了典型两亲性化合物1和2在水溶液中的自组装性质。对比研究表明,在自组装过程中,除了π-π堆积作用外,氢键和金属配位键的竞争和协同作用使得分子间不同的堆积模式进而得到不同的纳米形貌。四苯基卟啉分子间的强烈的π-π作用力使其聚集体形成一维的纳米带状形貌。分子间的π-π作用力和氢键的协同作用,使得化合物1其组装成纳米空心球。在化合物2的自组装过程中,除了分子间的π-π作用力和氢键的作用外,还有Cu-O金属配位键使其自组装得到一维的纳米线。这三个卟啉化合物在类似的自组装条件下,得到了不同形貌的纳米结构,这些研究结果表明非共价键尤其是π-π堆积、氢键和金属配位键的协同作用在调节和控制卟啉分子自组装纳米结构中起着非常重要的作用。这也为开发和探索新型的分子(光)电子器件的制备提供一条新的参考途径。
2、三明治型混杂卟啉酞菁三层稀土金属配合物的设计、合成和自组装纳米结构的研究
共轭分子体系自组装形成的各种不同结构稳定且复杂有序的纳米聚集体主要是通过分子间π-π键和其它非共价键的协同作用所得到的。所以,人们通常在共轭分子体系周围引入不同的功能基团来改变共轭分子的结构或者引入不同的非共价键来调节它们之间的作用进而调节自组装纳米结构的形貌。三明治型混杂卟啉酞菁稀土金属配合物由于在材料科学方面的应用引起了人们广泛和深入的研究兴趣。在这类化合物中,因为每个分子都有两到三个四吡咯环,并且每个四吡咯环上都有机会引入多样取代基,这样就大大增加了调节分子间作用力的可能性。所以,研究三明治型混杂卟啉酞菁稀土金属配合物的自组装过程对于它们在更多实际方面的应用提供理论价值。在本文中,我们首次详细的描述了一系列新型的三明治型混杂卟啉酞菁三层铕配合物的设计、合成、表征、以及它们的自组装性质。把不同数量或者相同数量不同位置的羟基引入到三明治型卟啉酞菁三层铕配合物卟啉的meso位苯环的对位上,在它们自组装过程中π-π堆积作用和由羟基提供的氢键的竞争和协同作用使得分子间不同的堆积模式进而得到不同的纳米形貌。在化合物1和2中,三明治分子间起到主导作用的π-π堆积作用,该作用力使其分别组装成纳米叶和线状形貌。在化合物4和5中,三明治分子间起到主导作用的是垂直于π-π堆积方向上的氢键,该作用力使其分别组装成弯曲的纳米带和球状形貌。然而,在化合物3中,氢键和π-π相互作用力的平衡使得化合物3组装成纳米带。本文工作不仅首次研究了分子结构和由其自组装得到相应的纳米结构之间的关系,而且对于通过分子设计和合成得到可控的分子堆积模式和纳米形貌有着很好的指导作用。
3、酚氧基和酚硫基在双层稀土酞菁配合物体系中取代基效应的研究
关于酚氧基或者酚硫基的电子性质已经成为大家争论的焦点。一般情况下,人们认为它们是类似与烷氧链和烷硫基链的供电子基,但是有时它们也可以作为吸电子基。在本文中,我们制备和表征了一系列酚氧基和酚硫基取代的的镧系双层酞菁配合物,电化学性质研究表明把八个酚氧基或者酚硫基引入到双层酞菁的周围后,使得化合物稍微的难于氧化但是易于还原,类似于化合物自由的H_2Pc(OPh)_4和H_2Pc(OPh)_8,表现出吸电子的性质。这一结论也被它们相应的自由酞菁基于前线分子轨道能量计算所支持。
Owing to the unique optical,electrical,and properties,associated with the intriguing intramolecularπ-πinteractions,porphyrins,phthalocyanines,as well as sandwich type rare complexes,as a novel functional materials,have been expected to be widely potential application in materials science,such as in molecular electronics,molecular information storage,and nonlinear optics,etc.Recently,it is significantly interested in ordered supramolecular aggregate and nanoscale assembly fields.However,it must be pointed out that self-assembly of functional molecules into a prerequisite nanostructure with desirable dimension and morphology via controlling and optimizing inter-molecular interaction still remains a great challenge for chemists and material scientists.In order to extensively investigate supramolecular aggregation behaviors and supramolecular assembly methodology of porphyrinato and/or phthalocyninato complexes,in this thesis a series of porphyrin and/or phthalocyanine derivatives are selected,and some modern measuring techniques were performed to examine their aggregate structures,morphologies and nanostructures.Our research work has been focused on the following respects:
1.Tuning the Morphology of Self-Assembled Nanostructures of Amphiphilic Tetra(p-hydroxyphenyl)Porphyrins with Hydrogen Bonding and Metal-Ligand Coordination Bonding
Typical amphiphilic metal free tetrakis(4-hydroxyphenyl)porphyrin H_2THPP(1) and tetrakis(4-hydroxyphenyl)porphyrinato copper complex CuTHPP(2) were fabricated into organic nanostructures by a phase-transfer method.Their self-assembly properties in aqueous solution have been comparatively studied with those of tetra(phenyl)porphyrin H_2TPP(3) by electronic absorption and Fourier transform infrared(FT-IR) spectroscopy, transmission electronic microscopy(TEM),scanning electronic microscopy(SEM),and X-ray diffraction(XRD) techniques.Experimental results reveal different molecular packing models in these aggregates,which in turn result in the self-assembled nanostructures with different morphology from nano-scale hollow spheres for 1,nanoribbons for 2,and to nanobelts for 3.The present study,representing part of our continuous efforts towards understanding the relationship between synergistic interplay among noncovalent interactions such as the n-n interaction,metal-ligand coordination bonding,and hydrogen bonding on controlling and tuning the morphology of self-assembled nanostructures of tetrapyrrole derivatives,will provide information helpful on preparing self-assembled nanostructures with controlled molecular packing conformation and morphology through molecular modification.
2.Morphology Controlled Self-assembled Nanostructures of Sandwich Mixed (Phthalocyaninato)(porphyrinato) Europium Triple-deckers.Effect of Hydrogen Bonding on Tuning the Inter-molecular Interaction
A series of five novel sandwich-type mixed(phthalocyaninato)(porphyrinato) europium triple-decker complexes with different number of hydroxyl groups at the meso-substituted phenyl groups of porphyrin ligand 1-5 have been designed,synthesized,and characterized. Their self-assembly properties,in particular the effects of the number and positions of hydroxyl groups on the morphology of self-assembled nanostructures of these triple-decker complexes,have been comparatively and systematically studied.Competition and cooperation between the inter-molecularπ-πinteraction and hydrogen bonding in the direction perpendicular to theπ-πinteraction direction for different compounds were revealed to result in nanostructures with different morphology from nano-leafs for 1, nano-fibbons for 2,nano-sheets for 3,curved nano-sheets for 4,and to spherical shapes for 5. The IR and X-ray diffraction(XRD) results reveal that in the nanostructures of triple-decker 2 as well as 3-5,a dimeric supramolecular structure was formed through an intermolecular hydrogen bond between two triple-decker molecules,which as the building block self-assembles into the target nanostructures.Electronic absorption spectroscopic results on the self-assembled nanostructures reveal the H-aggregate nature in the nano-leafs and nano-ribbons formed from triple-deckers 1 and 2 due to the dominantπ-πinter-molecular interaction between triple-decker molecules,but J-aggregate nature in the curved nano-sheets and spherical shapes of 4 and 5 depending on the dominant hydrogen bonding interaction in cooperation withπ-πinteraction among the triple-decker molecules.Electronic absorption and XRD investigation dearly reveal the decrease in theπ-πinteraction and increase in the hydrogen bonding interaction among triple-decker molecules in the nanostructures along with the increase of hydroxyl number in the order of 1-5.The present result appears to represent the first effort towards realization of controlling and tuning the morphology of self-assembled nanostructures of sandwich tetrapyrrole rare earth complexes through molecular design and synthesis.
3.Lanthanide(Ⅲ) Double-Decker Complexes with Octaphenoxy- or Octathiophenoxyphthalocyaninato Ligands.Revealing the Electron-Withdrawing Nature of the Phenoxy and Thiophenoxy Groups in the Double-Decker Complexes
A series of heteroleptic and homoleptic bis(phthalocyaninato) lanthanide(Ⅲ) complexes, namely M(Pc)[Pc(OPh)_8],M[Pc(OPh)_8]_2,Eu(Pc)[Pc(SPh)_8],and Eu[Pc(SPh)_8]_2[M = Eu,Ho, Lu;Pc = unsubstituted phthalocyaninate;Pc(OPh)_8 = 2,3,9,10,16,17,23,24-octaphenoxyphthalocyaninate;Pc(SPh)_8 = 2,3,9,10,16,17,23,24-octathiophenoxyphthalocyaninate](1-8) have been prepared.The molecular structure of Eu[Pc(OPh)_8]_2(4) has been determined by single-crystal X-ray diffraction analysis.All the new sandwich compounds have been characterized with various spectroscopic methods.Their electrochemical characteristics show that the introduction of phenoxy or thiophenoxy groups onto the peripheral positions of the phthalocyaninato ligand makes the double-decker harder to oxidize and easier to reduce.Theoretical calculations, using semi-empirical PM3 method,indicate that the change in the energy level of the frontier orbitals of these ligands induced by the electron-withdrawing substituents is responsible for these unusual electrochemical properties.
1、两亲性卟啉配合物自组装纳米结构的研究
有机功能分子自组装得到的有序纳米结构被预期在纳米科学与纳米技术中获得广泛的应用。自组装过程是一种自发的过程,是指分子间通过非共价键例如,氢键、配位键、堆积效应、静电相互作用、亲/疏水相互作用等形成的结构稳定、复杂有序且具有某种特定功能的纳米聚集体或超分子结构的过程。近十年来,通过分子的相互作用进行有机分子纳米结构自组装的研究一直是广大科研工作者研究的热点。各种各样形貌的有机纳米结构的报道层出不穷:纳米线、纳米棒、纳米颗粒和纳米管等等。然而,对化学家和材料学家来说,通过模拟和设计分子的结构调节分子间作用力以获得所希望的有机纳米结构材料的形貌仍然是一个挑战。在本章中,我们设计了三种卟啉分子Metal free tetrakis(4-hydroxyphenyl)porphyrin H_2THPP(1),Tetrakis(4-hydroxyphenyl)porphyrinato copper complex CuTHPP(2),和Metal freetetraphenylporphyrin H_2TPP(3)。利用相转移方法,把它们组装成有机纳米聚集体。参考化合物3利用紫外(UV)、红外(FT-IR)、透射电镜(TEM)、扫描电镜(SEM)、原子力显微镜(AFM)等表征手段系统研究了典型两亲性化合物1和2在水溶液中的自组装性质。对比研究表明,在自组装过程中,除了π-π堆积作用外,氢键和金属配位键的竞争和协同作用使得分子间不同的堆积模式进而得到不同的纳米形貌。四苯基卟啉分子间的强烈的π-π作用力使其聚集体形成一维的纳米带状形貌。分子间的π-π作用力和氢键的协同作用,使得化合物1其组装成纳米空心球。在化合物2的自组装过程中,除了分子间的π-π作用力和氢键的作用外,还有Cu-O金属配位键使其自组装得到一维的纳米线。这三个卟啉化合物在类似的自组装条件下,得到了不同形貌的纳米结构,这些研究结果表明非共价键尤其是π-π堆积、氢键和金属配位键的协同作用在调节和控制卟啉分子自组装纳米结构中起着非常重要的作用。这也为开发和探索新型的分子(光)电子器件的制备提供一条新的参考途径。
2、三明治型混杂卟啉酞菁三层稀土金属配合物的设计、合成和自组装纳米结构的研究
共轭分子体系自组装形成的各种不同结构稳定且复杂有序的纳米聚集体主要是通过分子间π-π键和其它非共价键的协同作用所得到的。所以,人们通常在共轭分子体系周围引入不同的功能基团来改变共轭分子的结构或者引入不同的非共价键来调节它们之间的作用进而调节自组装纳米结构的形貌。三明治型混杂卟啉酞菁稀土金属配合物由于在材料科学方面的应用引起了人们广泛和深入的研究兴趣。在这类化合物中,因为每个分子都有两到三个四吡咯环,并且每个四吡咯环上都有机会引入多样取代基,这样就大大增加了调节分子间作用力的可能性。所以,研究三明治型混杂卟啉酞菁稀土金属配合物的自组装过程对于它们在更多实际方面的应用提供理论价值。在本文中,我们首次详细的描述了一系列新型的三明治型混杂卟啉酞菁三层铕配合物的设计、合成、表征、以及它们的自组装性质。把不同数量或者相同数量不同位置的羟基引入到三明治型卟啉酞菁三层铕配合物卟啉的meso位苯环的对位上,在它们自组装过程中π-π堆积作用和由羟基提供的氢键的竞争和协同作用使得分子间不同的堆积模式进而得到不同的纳米形貌。在化合物1和2中,三明治分子间起到主导作用的π-π堆积作用,该作用力使其分别组装成纳米叶和线状形貌。在化合物4和5中,三明治分子间起到主导作用的是垂直于π-π堆积方向上的氢键,该作用力使其分别组装成弯曲的纳米带和球状形貌。然而,在化合物3中,氢键和π-π相互作用力的平衡使得化合物3组装成纳米带。本文工作不仅首次研究了分子结构和由其自组装得到相应的纳米结构之间的关系,而且对于通过分子设计和合成得到可控的分子堆积模式和纳米形貌有着很好的指导作用。
3、酚氧基和酚硫基在双层稀土酞菁配合物体系中取代基效应的研究
关于酚氧基或者酚硫基的电子性质已经成为大家争论的焦点。一般情况下,人们认为它们是类似与烷氧链和烷硫基链的供电子基,但是有时它们也可以作为吸电子基。在本文中,我们制备和表征了一系列酚氧基和酚硫基取代的的镧系双层酞菁配合物,电化学性质研究表明把八个酚氧基或者酚硫基引入到双层酞菁的周围后,使得化合物稍微的难于氧化但是易于还原,类似于化合物自由的H_2Pc(OPh)_4和H_2Pc(OPh)_8,表现出吸电子的性质。这一结论也被它们相应的自由酞菁基于前线分子轨道能量计算所支持。
Owing to the unique optical,electrical,and properties,associated with the intriguing intramolecularπ-πinteractions,porphyrins,phthalocyanines,as well as sandwich type rare complexes,as a novel functional materials,have been expected to be widely potential application in materials science,such as in molecular electronics,molecular information storage,and nonlinear optics,etc.Recently,it is significantly interested in ordered supramolecular aggregate and nanoscale assembly fields.However,it must be pointed out that self-assembly of functional molecules into a prerequisite nanostructure with desirable dimension and morphology via controlling and optimizing inter-molecular interaction still remains a great challenge for chemists and material scientists.In order to extensively investigate supramolecular aggregation behaviors and supramolecular assembly methodology of porphyrinato and/or phthalocyninato complexes,in this thesis a series of porphyrin and/or phthalocyanine derivatives are selected,and some modern measuring techniques were performed to examine their aggregate structures,morphologies and nanostructures.Our research work has been focused on the following respects:
1.Tuning the Morphology of Self-Assembled Nanostructures of Amphiphilic Tetra(p-hydroxyphenyl)Porphyrins with Hydrogen Bonding and Metal-Ligand Coordination Bonding
Typical amphiphilic metal free tetrakis(4-hydroxyphenyl)porphyrin H_2THPP(1) and tetrakis(4-hydroxyphenyl)porphyrinato copper complex CuTHPP(2) were fabricated into organic nanostructures by a phase-transfer method.Their self-assembly properties in aqueous solution have been comparatively studied with those of tetra(phenyl)porphyrin H_2TPP(3) by electronic absorption and Fourier transform infrared(FT-IR) spectroscopy, transmission electronic microscopy(TEM),scanning electronic microscopy(SEM),and X-ray diffraction(XRD) techniques.Experimental results reveal different molecular packing models in these aggregates,which in turn result in the self-assembled nanostructures with different morphology from nano-scale hollow spheres for 1,nanoribbons for 2,and to nanobelts for 3.The present study,representing part of our continuous efforts towards understanding the relationship between synergistic interplay among noncovalent interactions such as the n-n interaction,metal-ligand coordination bonding,and hydrogen bonding on controlling and tuning the morphology of self-assembled nanostructures of tetrapyrrole derivatives,will provide information helpful on preparing self-assembled nanostructures with controlled molecular packing conformation and morphology through molecular modification.
2.Morphology Controlled Self-assembled Nanostructures of Sandwich Mixed (Phthalocyaninato)(porphyrinato) Europium Triple-deckers.Effect of Hydrogen Bonding on Tuning the Inter-molecular Interaction
A series of five novel sandwich-type mixed(phthalocyaninato)(porphyrinato) europium triple-decker complexes with different number of hydroxyl groups at the meso-substituted phenyl groups of porphyrin ligand 1-5 have been designed,synthesized,and characterized. Their self-assembly properties,in particular the effects of the number and positions of hydroxyl groups on the morphology of self-assembled nanostructures of these triple-decker complexes,have been comparatively and systematically studied.Competition and cooperation between the inter-molecularπ-πinteraction and hydrogen bonding in the direction perpendicular to theπ-πinteraction direction for different compounds were revealed to result in nanostructures with different morphology from nano-leafs for 1, nano-fibbons for 2,nano-sheets for 3,curved nano-sheets for 4,and to spherical shapes for 5. The IR and X-ray diffraction(XRD) results reveal that in the nanostructures of triple-decker 2 as well as 3-5,a dimeric supramolecular structure was formed through an intermolecular hydrogen bond between two triple-decker molecules,which as the building block self-assembles into the target nanostructures.Electronic absorption spectroscopic results on the self-assembled nanostructures reveal the H-aggregate nature in the nano-leafs and nano-ribbons formed from triple-deckers 1 and 2 due to the dominantπ-πinter-molecular interaction between triple-decker molecules,but J-aggregate nature in the curved nano-sheets and spherical shapes of 4 and 5 depending on the dominant hydrogen bonding interaction in cooperation withπ-πinteraction among the triple-decker molecules.Electronic absorption and XRD investigation dearly reveal the decrease in theπ-πinteraction and increase in the hydrogen bonding interaction among triple-decker molecules in the nanostructures along with the increase of hydroxyl number in the order of 1-5.The present result appears to represent the first effort towards realization of controlling and tuning the morphology of self-assembled nanostructures of sandwich tetrapyrrole rare earth complexes through molecular design and synthesis.
3.Lanthanide(Ⅲ) Double-Decker Complexes with Octaphenoxy- or Octathiophenoxyphthalocyaninato Ligands.Revealing the Electron-Withdrawing Nature of the Phenoxy and Thiophenoxy Groups in the Double-Decker Complexes
A series of heteroleptic and homoleptic bis(phthalocyaninato) lanthanide(Ⅲ) complexes, namely M(Pc)[Pc(OPh)_8],M[Pc(OPh)_8]_2,Eu(Pc)[Pc(SPh)_8],and Eu[Pc(SPh)_8]_2[M = Eu,Ho, Lu;Pc = unsubstituted phthalocyaninate;Pc(OPh)_8 = 2,3,9,10,16,17,23,24-octaphenoxyphthalocyaninate;Pc(SPh)_8 = 2,3,9,10,16,17,23,24-octathiophenoxyphthalocyaninate](1-8) have been prepared.The molecular structure of Eu[Pc(OPh)_8]_2(4) has been determined by single-crystal X-ray diffraction analysis.All the new sandwich compounds have been characterized with various spectroscopic methods.Their electrochemical characteristics show that the introduction of phenoxy or thiophenoxy groups onto the peripheral positions of the phthalocyaninato ligand makes the double-decker harder to oxidize and easier to reduce.Theoretical calculations, using semi-empirical PM3 method,indicate that the change in the energy level of the frontier orbitals of these ligands induced by the electron-withdrawing substituents is responsible for these unusual electrochemical properties.
引文
[1]H.Ficsher et al.Die Chemic des pyrrols[M]Vol 2,part 1,Akademic Verlagsegesllschft,Liepzig,1937,158.
[2]J.Zelaski.Porphyrin[J]Z.Physiol.Chem.,1902,37,54.
[3]C.P.Wang et al.Lanthanide porphyrin complexes.Potential new class of nuclear magnetic resonance dipolar probe.[J]J.Am.Chem.Soc.,1974,96,7149-7150.
[4]C.P.Wang et al.Porphyrin complexes.[J]Tetrahydron Lett.,1975,31,237.
[5]计亮年,彭小彬,黄锦汪.金属卟啉配合物模拟某些金属酶的研究进展自然科学进展[J]2002,12,120-129.
[6]J.S.Sessler,S.J.Weghom.Expended,Contracted,81 isomeric porphyrins[M]Pergamon,Perface,1997.
[7]李德平,胡静.血卟啉类化合物诊治肿瘤的研究进展及应用[J]中国生化药物杂志,2003,24,162-163.
[8]杨新国,孙景志,汪茫,陈红征,黄骥.卟啉类光电功能材料研究进展[J]功能材料,2003,34,113-117.
[9](a) N.Uyeda,T.Kobayashi,E.Suito,Y.Harada,M.Watanabe.Molecular image resolution in electron microscopy[J]J.Appl.Phys.,1972,43,5181-5189.
(b) T.Kobayashi,S.Isoda.Lattice Images and Molecular Images of Organic Materials[J]J.Mater.Chem.1993,3,1-14.
[10]Eley,D.D.Phthalocyanines as semiconductors[J]Nature 1948,162,819-819.
[11](a) Schramm,C.J.,Stojakovic,D.R.,Hoffman,B.M.&Marks,T.J.;New low-dimensional molecular metals:single-crystal electrical conductivity of nickel phthalocyanine iodide[J]Science,1978,200,47.
(b) Marks,T.J.,Electrically conductive metallomacrocyclic assemblies;[J]Science,1985,227,881-889.
[12](a) Bott,B.,Jones,T.A.;A highly sensitive NO_2 sensor based on electrical conductivity changes in phthalocyanine films;[J]Sensors&Actuators,1984,5,43.
(b)Wright,J.D.;Gas adsorption on phthalocyanines and its effects on electrical properties.[J]Prog.Surf.Sci.1989,31,1.
[13]Vartanyan,A.T.Poluprovodnikovye Svoistva Organicheskikh Krasitel[J]Zh.Fiz Khim.948,22,769-774.
[14]Law,K.-Y.Organic photoconductive materials:recent trends and developments.[J]Chem.Rev.,1993,93,449-486
[15]Tang,C.W.;Two-layer organic photovoltaic cell;[J]Appl.Phys.Lett.,1986,48,183-185
[16]Nazeeruddin,M.K.,et al,Efficient near IR sensitization of nanocrystalline TiO_2films by ruthenium phthalocyanines.[J]Chem.Commun.,1998,719-720
[17]Wohrle,D.,et al,Microlasers based on organic dyes in nanoporous crystals[J]Molecular Crystals&Liquid Crystals,1993,230,221.
[18]王朝晖,衷庆华,熊轶嘉,孙亚,孔繁敖.酞菁锌分子激发态的超快内转换和振动弛豫[J]化学物理学报,1998,2,15-18.
[19]De la Torre,G,Vazquez.P.et al.Phthalocyanines and related compounds.[J]J.Mater Chem.,1998,8,1671-1683.
[20]Shirk J.S.,Lindle J.R.,Bartoli F.J.et al.Third-order optical nonlinearities of bis(phthalocyanines)[J]J.Phys.Chem.,1992,96,5847-5852.
[21]陈仕艳,刘云圻,黄学斌,邱文丰,朱道本.酞菁在分子材料器件方面的研究进展[J]自然科学进展,2004,14,125-132.
[22]C.C.Leznoff,A.B.P.Lever.Phthalocynines:properties and applications.[M]Volumes 1-4,New York:VCH,1989.
[23]Borisenkova,S.A.New aspects of the heterogeneous catalysis of thiol oxidation by phthalocyanines.[J]Petroleum Chem.1991,31,379-398.
[24]Bennett W.E.,Broberg D.E.,Baenziger N.C.Crystal structure of stannic phthalocyanine,an eight-coordinated tin complex[J]Inorg.Chem.1973,12,930-936.
[25]Kirin I.S.,Moskalev E N.,Makashev Yu.A.Formation of phthalocyanines of rare-earth elements[J]Russ.J.Inorg.Chem.1965,10,1065.
[26]Cian A.De.,Moussavi M.,Fischer J.et al.,Synthesis,structure,and spectroscopic and magnetic properties of lutetium(Ⅲ) phthalocyanine derivatives[J]Inorg.Chem.,1985,24,3162-3167.
[27](a) Lux F.,Dempf D.,Graw D.,Diphthalocyaninato-thorium(Ⅳ) and-uranium(Ⅳ)[J]Angew.Chem.Int.Ed.Eng.,1968,7,819-820.
(b) Lux,F.,Brwon,D.,Dempf,D.et al.Synthesis of 1-Adamantanecarbaldehydes.[J]Angew.Chem.Int.Ed.Eng.1969,7,894.
[28]M.Bouvet,J.Smion,Electrical properties of rare earth bisphthalocyanine and bisnaphthalocyanine complexes.[J]Chem.Phys.Lett.1990,172,299
[29]D.K.P.Ng,J.Jiang.,Sandwich-Type Heteroleptic Phthalocyaninato and Porphyrinato Metal Complexes[J]Chem.Soc.Rev.1997,26,433-442.
[30]姜建壮,吴基培,刘伟,谢经雷,孙思修.对称的二层及三层三明治型金属酞菁配合物的研究进展.[J]化学通报.1999,2.
[31]A.Gieren,W.Hoppe,X-Ray crystal structure analysis of bisphthalocy aninatouranium[J]Chem.Commun.1971,413.
[32]Cian.A.De;Moussavi M;Fischer J;et al.;Synthesis,structure,and spectroscopic and magnetic properties of lutetium(Ⅲ) phthalocyanine derivatives[J]Inorg.Chem.1985,24,3162.
[33]Koike.N.,Uekusa.H.,Ohashi Y.;et al.;Relationship between the Skew Angle and Interplanar Distance in Four Bis(phthalocyaninato)lanthanide(Ⅲ) Tetrabutyl ammonium Salts([NBun_4][LnPc_2];Ln=Nd,Gd,Ho,Lu)[J]Inorg.Chem.1996,35,5798.
[34]J.Buchler,A.D.C.J.Fischer;M.K.Botulinski;H.Paulus;R.Weiss.;Metal complexes with tetrapyrrole ligands.Cerium(Ⅳ) bis-(octaethylporphyrinate) and dicerium(Ⅲ) tris(oetaethylporphyrinate):Parents of a new family of lanthanoid double-decker and triple-decker molecules;[J]J.Am.Soc.1986,108;3652.
[35]G.C.S.Collins;D.J.Schiffrin;The electrochromic properties of lutetium and other phthalocyanines.[J]J.Electroanal.Chem.1982,139,335.
[36]C.S.Frampton;J.M.O'Connor;J.Peterson;J.Silver,Enhanced colors and properties in the electrochromic behavior of mixed rare-earth-element bisphthalcoyanines.[J]Displays,1988,9,174.
[37]A.Capobianchi,A.M.Paoletti,G.Pennesi,G.Rossiand S.Paner;Electrochromism in sandwich-type diphthalocyanines:electrochemical and spectroscopic behaviour of bis(phthalocyaninato)titanium(Ⅳ)(Ti(Pc)_2) film.[J]Synth.Met.1995,75,37.
[38]McKeown,N.B.;The general chemistry of phthalcoyanines.[J]Chem.& Industry;1999,Feb.1,92.
[39]J.J.Andre,K.Holczer,P.Petit,M.T.Riou,J.Smon;Electrical and magnetic properties of thin films and single crystals of bis(phthalocyaninato) lutetium.[J]Chem.Phys.Lett.1985,115,463.
[40]J.Padilla and W.E.Hatifield.Magnetic and electrical properties of sandwich-like lanthanide phthalocyanines;[J]Synth.Met.1989,29,F45.
[41]J.Padilla and W.E.Hatifield;Correlation between π-orbital overlap and conductivity in bis-phthalocyaninato lanthanides;[J]Inorg.Chim.Acta.1991,185.131.
[42]J.Souto,R.Aroca,J.A.Desaja;Gas Adsorption and Electrical Conductivity of Langrnuir-Blodgett Films of Terbium Bisphthalocyanine.[J]J.Phys.Chem.1994,98,8998.
[43]M.Trometer,R.Even,J.Simon,A.Dubon and J.-Y.LavalJ.P.Germain,C.Maleysson,A.Pauly and H.Robert;Lutetium bisphthalocyanine thin films for gas detection.[J]Sens.Actuators B.1992,8,129.
[44]J.Simon and S.Sidin;Mesomorphic molecular materials for electronics,optoelectronics,iono-electronics:octaalkylphthalocyanine derivatives[J]Pure Appl.Chem.1989,61,1625.
[45]G.Guillaud,M.Al Sadoun,M.Maitrot,J.J.Andre,J.Simon and R.Even.Field-effect transistors based on intrinsic molecular semiconductors[J]Chem.Phys.Lett.1988,167,503.
[46]C.Clarisse,M.T.Riou,M.Gauneau and M.Le Cntellec.Field-Effect Transistor with Diphthalocyanine Thin Film[J]Electron.Lett.1988,24,674.
[47]T.Toupance,V.Ahsen and J.Simon.Iono-electronics:crown ether substituted lutetium bisphthalocyanines[J]J.Chem.Soc.,Chem.Commun.1994,75-76.
[48]Nicholson M.M,Pizzarello F.A.The redox chemistry of phthalocyanine[J]J.Electrochem Soc,1980,127,2617.
[49]Nicholson M.M,Pizzarello F.A.;The role of oxygen in the redox chemistry of luterrium diphthalocyanine;[J]J.Electrochem Soc,1984,131,2311.
[50]K.L.Trojan,J.L.Kendall,K.D.Kepler and W.E.Hatfield;Strong exchange coupling between the lanthanide ions and the phthalocyaninato ligand radical in bis(phthalocyaninato)lanthanide sandwich compounds[J]Inorg.Chim.Acta.1992,198,795.
[51](a) Lehn J.M.Supramolecular Chemistry-Concepts and Perspectives.[M]Weinheim:VCH Publishers,1995;
(b)V(o|¨)gtle F.著.张希,林志宏,高倩译,超分子化学.[M]长春:吉林大学出版社,1995:
(c)Ringsdorf,H.;Schlarb,B.:Venzmer J.Molecular architecture and function in polymeric oriented systems:models for the study of organization,surface recognition,and dynamics in biomembranes.[J]Angew.Chem.Int.Ed.1998,27,113;
(d) Zhang,X.;Shen,J.C.self-assembled ultrathin films:from layered nanoarchitectures to functional assemblies.[J]Adv.Mater.,1999,11,1139.
[52]Vogtle,F.Supramolekulare Chemic,[M]Teubner,Stuttgart,1991.
[53](a) Cram.D.J.The Design of Molecular Hosts,Guests,and Their Complexes;[J]Angew.Chem.Int.Ed.1988,27,1009-1020.
(b) Lehn,J.-M.Supramolecular Chemistry-Scope and Perspectives Molecules,Supermolecules,and Molecular Devices;[J]Angew.Chem.Int.Ed.1988,27,89-112.
[54](a) Lehn,J.-M.Perspectives in Supramolecular Chemistry-From Molecular Recognition towards Molecular Information Processing and Self-Organization.[J]Angew.Chem.Int.Ed.1990,29,1304-1319.
(b) Lehn,J.-M.Supramolecular chemistry.[J]Science 1993,260,1762-1763.
(c) Lehn,J.-M.Supramolecular Chemistry:Concepts and Perspectives;[M]VHC,Weinheim,1995.
[55]Lehn J.M.Programmed Chemical Systems:Multiple Subprograms and Multiple Processing/Expression of Molecular Information.[J]Chem.Eur.J.,2000,6,2097-2102.
[56]吴世康编著,超分子光化学导论,[M]北京 科学出版社,2005.
[57](a) Balzani,V.;Credi,A.;Raymo,F.M.;Stoddart,J.F.Artificial Molecular Machines.[J]Angew.Chem.Int.Ed,2000,39,3348-3391.
(b) 刘育,尤长城,张衡益著 超分子化学-合成受体的分子识别与组装[M]天津 南开大学出版社,2001.
[58]刘海洋,胡希明,应晓,刘义,黄锦汪,计亮年,金属卟啉配合物超分子弹自组装.[J]无机化学学报,1998,14,371-387.
[59]Drain,C.M.,Lehn,J.M.,[J]J.Chem.Soc.Chem.Commun.,1994,2313-2314.
[60]Drain,C.M.;Nifiatis,F.;Vasenko,A.;Batteas,J.D.Porphyrin Tessellation by Design:Metal-Mediated Self-Assembly of Large Arrays and Tapes.[J]Angew.Chem.Int.Ed.,1998,37,2344-2347.
[61]Engelkamp,H.;Middelbeek,S.;Nolte,R.J.M.Self-Assembly of Disk-Shaped Molecules to Coiled-Coil Aggregates with Tunable Helicity.[J]Science,1999,284,785-788
[62](a) Shirakawa,M.;Fujita,N.;Shinkai,S.A Stable Single Piece of Unimolecularly π-Stacked Porphyrin Aggregate in a Thixotropic Low Molecular Weight Gel:A One-Dimensional Molecular Template for Polydiacetylene Wiring up to Several Tens of Micrometers in Length.[J]J.Am.Chem.Soc.2005,127,4164-4165.
(b) Kishida,T.;Fujita,N.;Sada,K.;Shinkai,S.Sol-Gel Reaction of Porphyrin-Based Superstructures in the Organogel Phase:Creation of Mechanically Reinforced Porphyrin Hybrids.[J]J.Am.Chem.Soc.2005,127,7298-7299.
(c) Shirakawa,M.;Fujita,N.;Shinkai,S.[60]Fullerene-Motivated Organogel Formation in a Porphyrin Derivative Bearing Programmed Hydrogen-Bonding Sites.[J]J.Am.Chem.Soc.2003,125,9902-9903.
(d) Sano,M.;Kamino,A.;Okamura,J.;Shinkai,S.Self-Organization of PEO-graft-Single-Walled Carbon Nanotubes in Solutions and Langmuir-Blodgett Films.[J]Langmuir,2001,17,5125-5128.
[63]Tamaru S.I.;Nakamuira,M.;Takeuchi M.;Shinkai S.Rational Design of a Sugar-Appended Porphyrin Gelator That Is Forced To Assemble into a One-Dimensional Aggregate.[J]Org.Lett.,2001,3,3631-3634.
[64]Ayabe,M.;Yamashita,K.;Shinkai,S.;Ikeda,A.;Sakamoto,S.;Yamaguchi,K.Construction of Monomeric and Polymeric Porphyrin Compartments by a Pd(Ⅱ)-Pyridine Interaction and Their Chiral Twisting by a BINAP Ligand.[J]J.Org.Chem.,2003,68,1059-1066.
[65]Hu,J.-S.;Guo,Y.-G.;Liang,H.-P.;Wan,L.-J.;Jiang,L.Three-Dimensional Self-Organization of Supramolecular Self-Assembled Porphyrin Hollow Hexagonal Nanoprisms.[J]J.Am.Chem.Soc.2005,127,17090-17095.
[66](a) Wang,Z.;Medforth,C.J.;Shelnutt,J.A.Porphyrin Nanotubes by Ionic Self-Assembly.[J]J.Am.Chem.Soc.,2004,126,15954-15955.
(b) Wang,Z.;Medforth,C.J.;Shelnutt,J.A.Self-Metallization of Photocatalytic Porphyrin Nanotubes.[J]J.Am.Chem.Soc.,2004,126,16720-16721.
[67]Gong,X.;Milic,T.;Xu,C.;Batteas,J.D.;Drain,C.M.Preparation and Characterization of Porphyrin Nanoparticles.[J]J.Am.Chem.Soc.2002,124,14290-14291.
[68](a) Kimura,M.;Muto,T.;Takimoto,H.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai.H.;Kobayash,N.Fibrous Assemblies Made of Amphiphilic Metallophthalocyanines.[J]Langmuir 2000,16,2078-2082.
(b) Kimura,M.;Kuroda,T.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Self-Organization of Hydrogen-Bonded Optically Active Phthalocyanine Dimers.[J]Langmuir 2003,19,4825-4830.
[69](a) Nitschke,C.;O'Flaherty,S.M.;Kroll,M.;Blau,W.J.Material Investigations and Optical Properties of Phthalocyanine Nanoparticles.[J]J.Phys.Chem.B.,2004,108,1287-1295.
(b) Zhang,X.;Wang,Y.;Ma,Y.;Ye,Y.;Wang,Y.;Wu,K.Solvent-Stabilized Oxovanadium Phthalocyanine Nanoparticles and Their Application in Xerographic Photoreceptors.[J]Langmuir,2006,22,344-348.
[70]K.Ishii,Y.Ohba,M.Iwaizumi and S.Yamauch,Studies on Monomers and Dimers of Y(Ⅲ) and La(Ⅲ) Porphyrin Complexes by Time-Resolved Electron Paramagnetic Resonance[J]J.Phys.Chem.1996,100,3839-3846.
[71]H.Konami,M.Hatano,N.Kobayashi and T.Osa.Redox potentials of a series of lanthanide-bisphthalocyanine sandwich complexes.[J]Chem.Phys.Lett.1990,165,397-400.
[72]J.Padilla and W.E.Hatfield,σ and π-interactions of the pyrrolillc ligand of sandwich-like lanthanide phthalocyanines determined from magnetic susceptibility and ligand-field theory.[J]Inorg.Chim.Acta,1990,172,241.
[73]E.Oriti,J.L.Bredas and C.Clarisse,Studies on Monomers and Dimers of Y(Ⅲ) and La(Ⅲ) Porphyrin Complexes by Time-Resolved Electron Paramagnetic Resonance;[J]J.Chem.Phys.1990,92,1228.
[74]P.C.Martin,J.Arnold,and D.F.Bocian;Spectroscopic characterization of zirconium (Ⅳ) and hafnium(Ⅳ) sandwich porphyrin complexes;[J]J.Phys.Chem.1993,97,1332
[75]J.W.Buchler and B.Scharbert,Metal complexes with tetrapyrrole ligands.50.Redox potentials of sandwichlike metal bis(octaethylporphyrinates) and their correlation with ring-ring distances.[J]J.Am.Chem.Soc.1988,110,4272-4278.
[76]J.Jiang,W.Liu,-F.Law,and D.K.P.Ng;A new synthetic route to unsymmetrical bis (phthalocyaninato)europium(Ⅲ) complexes.[J]Inorg.Chim.Acta,1998,268,141-144.
[1]Schouten,P.G.;Warman,J.M.;de Haas,M.P.;Fox,M.A.;.Pan,H.L.Charge migration in supramolecular stacks of peripherally substituted porphyrins.[J]Nature 1991,353,736-737.
[2]J.-M.Lehn,Toward Self-Organization and Complex Matter.[J]Science 2002,295,2400-2403.
[3]Gan,H.;Liu,H.;Li,Y.;Zhao,Q.;Li,Y.;Wang,S.;Jiu,T.;Wang,N.;He,X.;Yu,D.;Zhu,D,Fabrication of Polydiacetylene Nanowires by Associated Self-Polymerization and Self-Assembly Processes for Efficient Field Emission Properties.[J]J.Am.Soc.Chem.2005,127,12452-12453.
[4]Balakrishnan,K.;Datar,A.;Naddo,T.;Huang,J.;Oitker,R.;Yen,M.;Zhao,J.;Zang,L.Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules:Morphology Control.[J]J.Am.Chem.Soc.2006,128,7390-7398.
[5]Vriezema,D.M.;Hoogboom,J.;Velonia,K.;Takazawa,K.;Christianen,P.C.M.;Maan,J.C.;Rowan,A.E.;Nolte,R.J.M.Vesicles and Polymerized Vesicles from hiophene-Containing Rod-Coil Block Copolymers.[J]Angew.Chem.Int.Ed.2003,42,772-776.
[6](a) Yan,D.Y.;Zhou,Y.F.;Hou,J.Supramolecular Self-Assembly of Macroscopic Tubes.[J]Science 2004,303,65-67.
(b) Hu,J.-S.;Guo,Y.-G.;Liang,H.-P.;Wan,L.-J.;Jiang,L.Three-Dimensional Self-Organization of Supramolecular Self-Assembled Porphyrin Hollow Hexagonal Nanoprisms.[J]J.Am.Chem.Soc.2005,127,17090-17095.
(c) Shimizu,T.;Masuda,M.;Minamikawa,H.Supramolecular Nanotube Architectures Based on Amphiphilic Molecules.[J]Chem.Rev.2005,105,1401-1444.
(d) Zhi,L.;Gorelik,T.;Wu,J.;Kolb,U.;M(u|¨)llen,K.Nanotubes Fabricated from Ni-Naphthalocyanine by a Template Method.[J]J.Am.Chem.Soc.2005,127,12792-12793.
(e) Liu,Q.;Li,Y.;Liu,H.;Chen,Y.;Wang,X.;Zhang,Y.;Li,X.;Jiang,J.Nanotubes Fabricated from Sandwich-Type Mixed(Porphryinato)(phthalocyaninato)europium Complex by Template Technique.[J]J.Phys.Chem.C.2007,111,7298-7301.
[7]Charvet,R.;Jiang,D.L.;Aida,T.Self-assembly of a n-electronic amphiphile consisting of a zinc porphyrin-fullerene dyad:formation of micro-vesicles with a high stability.[J]Chem.Commun.2004,2664-2665.
[8]Li,Y.;Li,X.;Li,Y:Liu,H.;Wang,S.;Gan,H.;Li,J.;Wang,N.;He,X.;Zhu,D.Controlled Self-Assembly Behavior of an Amphiphilic Bisporphyrin-Bipyridinium-Palladium Complex:From Multibilayer Vesicles to Hollow Capsules.[J]Angew.Chem.Int.Ed.2006,45,3639-3643.
[9](a) Zupan,K.;Herenyi,L.;Toth,K.;Majer,Z.;Csik,G.Binding of Cationic Porphyrin to Isolated and Encapsidated Viral DNA Analyzed by Comprehensive Spectroscopic Methods.[J]Biochemistry,2004,43,9151-9159.
(b) Zupan,K.;Herenyi,L.;Toth,K.;Egyeki,M.;Csik,G.Binding of Cationic Porphyrin to Isolated DNA and Nucleoprotein Complex:Quantitative Analysis of Binding Forms under Various Experimental Conditions.[J]Biochemistry,2005,44,15000-15006.
[10]Stang,P.J.;Olenyuk,B.Self-Assembly,Symmetry,and Molecular Architecture:Coordination as the Motif in the Rational Design of Supramolecular Metallacyclic Polygons and Polyhedra.Acc.Chem.Res.[J]1997,30,502-518.
[11](a) Imamura,T.;Fukushima,K.Self-assembly of metallopyridylporphyrin oligomers.[J]Coord.Chem.Rev.2000,198,133-156.
(b) Wojaczynski,J.;Latos-Grazynski,L.Poly- and oligometalloporphyrins associated through coordination.[J]Coord.Chem.Rev.2000,204,113-171.
[12]Suslick,K.S.;Bhyrappa,P.;Chou,J.-H.;Kosal,M.E.;Nakagaki,S.;Smithenry,D.W.;Wilson,S.R.Microporous Porphyrin Solids.[J]Acc.Chem.Res.2005,38,283-291.
[13]Yu,J.Mathew,S.Flavel,B.S.Johnston,M.R.Shapter,J.G.Ruthenium Porphyrin Functionalized Single-Walled Carbon Nanotube ArrayssA Step Toward Light Harvesting Antenna and Multibit Information Storage.[J]J.Am.Chem.Soc.2008,130,8788-8796.
[14]Takahashi,R.;Kobuke,Y.Hexameric Macroring of Gable-Porphyrins as a Light-Harvesting Antenna Mimic.[J]J.Am.Chem.Soc.2003,125,2372-2373.
[15]Kosal,M.E.;Chou,J.-H.;Wilson,S.R.;Suslick,K.S.[J]Nat.Mater.2002,1,118-121.
[16]Van Nostrum,C.F.;Nolte,R.J.M.Functional supramolecular materials:self-assembly of phthalocyanines and porphyrazines.[J]Chem.Commun.1996, 2385-2392.
[17]Engelkamp,H.;Middelbeek,S.;Nolte,R.J.M.Self-Assembly of Disk-Shaped Molecules to Coiled-Coil Aggregates with Tunable Helicity.[J]Science 1999,284,785-788.
[18]Elemans,J.A.A.W.;Rowan,A.E.;Nolte,R.J.M.Mastering molecular matter.Supramolecular architectures by hierarchical self-assembly.[J]J.Mater.Chem.2003,13,2661-2670.
[19]Samori,P.;Engelkamp,H.;de Witte,P.;Rowan,A.E.;Nolte,R.J.M.Rabe,J.P.Self-Assembly and Manipulation of Crown Ether Phthalocyanines at the Gel-Graphite Interface.[J]Angew.Chem.Int.Ed.2001,40,2348-2350.
[20]Samori,P.;Engelkamp,H.;de Witte,P.A.J.;Rowan,A.E.;Nolte,R.J.M.;Rabe,J.P.Self-Organization of Semiconducting Polysiloxane-Phthalocyanine on a Graphite Surface.[J]Adv.Mater.2005,17,1265-1268.
[21]Sly,J.;Kasak,P.Gomar-Nadal,E.;Rovira,C.;Gorriz,L.;Thordarson,P.;Amabilino,D.B.;Rowan,A.E.;Nolte,R.J.M.Chiral molecular tapes from novel tetra(thiafulvalene-crown-ether)-substituted phthalocyanine building blocks.[J]Chem.Commun.2005,1255-1257.
[22]Lu,G.;Chen,Y.;Zhang,Y.;Bao,M.;Bian,Y.;Li,X.;Jiang,J.Morphology Controlled Self-assembled Nanostructures of Sandwich Mixed (Phthalocyaninato)(porphyrinato) Europium Triple-deckers.Effect of Hydrogen Bonding on Tuning the Inter-molecular Interaction.[J]J.Am.Chem.Soc.2008,130,11623-11630.
[23]Gao,Y.;Zhang,X.;Ma.C.;Li,X.;Jiang,J.Morphology Controlled Self-assembled Nanostructures of 5,15-Di[4-(5-acetylsulfanylpentyloxy)phenyl]porphyrin Derivatives.Effect of Metal-Ligand Coordination Bonding on Tuning the Inter-molecular Interaction.[J]J.Am.Chem.Soc.2008,130,17044-17052.
[24]Konan,Y.N.;Cerny,R.;Favet,J.;Berton.M.;Gurny,R.;Allemann,E.Preparation and characterization of sterile sub-200 nm meso-tetra(4-hydroxylphenyl)porphyrin-loaded nanoparticles for photodynamic therapy.[J]Eur.J.Pharm.Biopharm.2003,55,115-124.
[25]Konan,Y.N.;Berton.M.;Gurny,R.;Allemann,E.Enhanced photodynamic activity of meso-tetra(4-hydroxyphenyl)porphyrin by incorporation into sub-200nm nanoparticles.[J]Eur.J.Pharm.Science.2003,18,241-249.
[26](a) Adler,A.D.;Longo,F.R.;Shergalis.W.Mechanistic Investigations of Porphyrin Syntheses.I.Preliminary Studies on ms-Tetraphenylporphinl.[J]J.Am.Chem.Soc.,1964,86,3145-3149.
(b) Adler,A.D.;Longo,F.R.;Finarelli,J.D.;Goldmacher,J.;Assour,J.;Korsakoff,L.A Simplified Synthesisfor msso-Tetraphenylporphin.[J]J.Org.Chem.1967,32,476-476.
[27](a) Guo,H.;Jiang,J.;Shi,Y.;Wang,Y.;Liu,J.;Dong,S.UV-Vis Spectrophotometric Titrations and Vibrational Spectroscopic Characterization of meso-(p-Hydroxyphenyl)porphyrins.[J]J.Phys.Chem.B.2004,108,10185-10191.
(b) Guo,H.;Jiang,J.;Shi,Y.;Wang,Y.;Wang,Y.;Dong,S.Sequential Deprotonation of meso-(p-Hydroxyphenyl)porphyrins in DMF:From Hyperporphyrins to Sodium Porphyrin Complexes.[J]J Phys.Chem.B.2006,110,587-594.
[28]Adler,A.D.;Longo,F.R.[J]J.Inorg.Nucl.Chem.1970,32,2443-2445.
[29](a) Gong,X.;Milic,T.;Xu,C.;Batteas,J.D.;Drain,C.M.Preparation and Characterization of Porphyrin Nanoparticles.[J]J.Am.Chem.Soc.2002,124,14290-14291.
(b) Maiti,N.C.;Mazumdar,S.;Periasamy,N,J- and H-Aggregates of Porphyrin-Surfactant Complexes:Time-Resolved Fluorescence and Other Spectroscopic Studies.[J]J.Phys.Chem.B 1998,102,1528-1538.
(c) Hunter,C.A.;Sanders,J.K.M.The Nature of π-π Interactions.[J]J.Am.Chem.Soc.1990,112,5525-5534.
(d) Kano,K.;Minamizono,H.;Kitae,T.;Negi,S.Self-Aggregation of Cationic Porphyrins in Water.Can(?)-(?) Stacking Interaction Overcome Electrostatic Repulsive Force.[J]J.Phys.Chem.A 1997,101,6118-6124.
(e) Purrello,R.;Monsu' Scolaro,L.;Bellacchio,E.;Gurrieri,S.;Romeo,A.Chiral H- and J-Type Aggregates of meso-Tetrakis(4-sulfonatophenyl)porphine on a-Helical Polyglutamic Acid Induced by Cationic Porphyrins.[J]Inorg.Chem.1998,37,3647-3648.
[30]Ulman,A.;Manassen,J.Synthesis of new tetraphenylporphyrin molecules containing heteroatoms other than nitrogen.I.Tetraphenyl-21,23-dithiaporphyrin.[J]J.Am.Chem.Soc.1975,97,6540-6544.
[31]Kasha,M.;Rawls,H.R.;EI-Bayoumi,M.A.[J]Pure Appl.Chem.1965,11, 371-392.
[32]Kano,K.;Fukuda,K.;Wakami,H.;Nishiyabu,R.;Pasternack,R.F.Factors Influencing Self-Aggregation Tendencies of Cationic Porphyrins in Aqueous Solution[J]J.Am.Chem.Soc.2000,122,7494-7502.
[33](a) Kimura,M.;Muto,T.;Takimoto,H.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai.H.;Kobayash,N.Fibrous Assemblies Made of Amphiphilic Metallophthalocyanines[J]Langmuir 2000,16,2078-2082.
(b) Kimura,M.;Kuroda,T.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Self-Organization of Hydrogen-Bonded Optically Active Phthalocyanine Dimers.[J]Langmuir 2003,19,4825-4830.
[34]Pan,J.;Nguyen,K.L.[J]Anal.Chem.2007,79,2259-2265.Sayed,M.B.[J]Ind.Eng.Chem.Res.2004,43,4822-4826.
[35]Balaban,T.S.;Linke-Schaetzel,M.;Bhise,A.D.;Vanthuyne,N.;Roussel,C.;Anson,C,E.;Buth,G.;Eichhofer,A.;Foster,K.;Garab,G.;Gliemann,H.;Goddard,R.;Javorfi,T.;Powell,A.K.;Rosner,H.;Schimmel,T.Structural Characterization of Artificial Self-Assembling Porphyrins That Mimic the Natural Chlorosomal Bacteriochlorophylls c,d,and e.[J]Chem.Eur.J.2005,11,2267-2275.
[36](a) Caruso,F.;Caruso,A.R.;M(o|¨)hwald,H.Nanoengineering of Inorganic and Hybrid Hollow Spheres by Colloidal Templating.[J]Science 1998,282,1111-1114.
(b) Caruso,F.Nanoengineering of Particle Surfaces.[J]Adv.Mater.2001,13,11-22.
(c) Ma,Y.R.;Qi,L.M.;Ma,J.M.;Cheng,H.M.Facile Synthesis of Hollow ZnS Nanospheres in Block Copolymer Solutions.[J]Langmuir 2003,19,4040-4042.
(d) Nakashima,T.;Kimizuka,N.Interracial Synthesis of Hollow TiO_2Microspheres in Ionic Liquids.[J]J.Am.Chem.Soc.2003,125,6386-6387.
[37]Kano,K.;Fukuda,K.;Wakami,H.;Nishiyabu,R.;Pasternack,R.F.Factors Influencing Self-Aggregation Tendencies of Cationic Porphyrins in Aqueous Solution.[J]J.Am.Chem.Soc.2000,122,7494-7502.
[38]Minch,B.A.;Xia,W.;Donley,C.L.;Hernandez,R.M.;Carter,C.;Carducci,M.D.;Dawson,A.;O'Brien,D.F.;Armstrong,N.R.Octakis(2-benzyloxyethylsulfanyl) Copper(Ⅱ) Phthalocyanine:A New Liquid Crystalline Discotic Material with Benzyl-Terminated,Thioether-Linked Side Chains.[J]Chem.Mater.2005,17,1618-1627.
[39]Belarbi,Z.;Sirlin,C.;Simon,J.;Andre,J.J.[J]J.Phys.Chem.1989,93,8105-8110.
[40]Kimura,M.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Organic-Inorganic Composites Comprised of Ordered Stacks of Amphiphilic Molecular Disks.[J]J.Am.Chem.Soc.2001,123,2438-2439.
[41]Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Montgomery,J.A.,Jr.;Vreven,T.;Kudin,K.N.;Burant,J.C.;Millam,J.M.;Iyengar,S.S.;Tomasi,J.;Barone,V.;Mennucci,B.;Cossi,M.;Scalmani,G.;Rega,N.;Petersson,G.A.;Nakatsuji,H.;Hada,M.;Ehara,M.;Toyota,K.;Fukuda,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Klene,M.;Li,X.;Knox,J.E.;Hratchian,H.P.;Cross,J.B.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Ayala,P.Y.;Morokuma,K.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Zakrzewski,V.G.;Dapprich,S.;Daniels,A.D.;Strain,M.C.;Farkas,O.;Malick,D.,K.;Rabuck,A.D.;Raghavachari,K.;Foresman,J.B.;Ortiz,J.V.;Cui,Q.;Baboul,A.G.;Clifford,S.;Cioslowski,J.;Stefanov,B.B.;Liu,G.;Liashenko,A.;Piskorz,P.;Komaromi,I.;Martin,R.L.;Fox,D.J.;Keith,T.;Al-Laham,M.A.;Peng,C.Y.;Nanayakkara,A.;Challacombe,M.;Gill,P.M.W.;Johnson,B.;Chen,W.;Wong,M.W.;Gonzalez,C.;Pople,J.A.Gaussian 03,Revision B.05;Gaussian,Inc.:Pittsburgh,PA,2003.
[42](a) Diskin-Posner,Y.;Patra,G.K.;Goldberg,I.Supramolecular porphyrin-based materials.Assembly modes of [5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrinato]zinc with bipyridyl ligands.[J]CrystEngComm.2002,4,296-301.
(b) Krishna Kumar,R.;Balasubramanian,S.;Goldberg,I.Supramolecular Multiporphyrin Architecture.Coordination Polymers and Open Networks in Crystals of Tetrakis(4-cyanophenyl)- and Tetrakis(4-nitrophenyl)metalloporphyrin.[J]Inorg.Chem.1998,37,541-552.
(c)Mazzanti,M.;Veyrat,M.;Ramasseul,R.;Marchon,J.-C.;Turowska-Tyrk,I.;Shang,M.;Scheidt,W.R.A New Ruthenium(Ⅱ) Chiroporphyrin Containing a Multipoint Recognition Site:Enantioselective Receptor of Chiral Aliphatic Alcohols.[J]Inorg.Chem.1996,35,3733-3734.
(d) Barkigia,K.M.;Rennet,M.W.;Senge,M.O.;Fajer,J.Interplay of Axial Ligation,Hydrogen Bonding, Self-Assembly,and Conformational Landscapes in High-Spin Ni(Ⅱ) Porphyrins[J]J.Phys.Chem.B.2004,108,2173-2180.
[43]Antonietti,M.;F(O|¨)rster,S.Vesicles and Liposomes:A Self-Assembly Principle Beyond Lipids.[J]Adv.Mater.2003,15,1323-1333.
[44]Yang,Y.-F.;Ma,Y.-S.;Guo,L.-R.;Zheng,L.-M.Copper Phosphonates based on 2-Phosphonic-isonicotinate:Structures and Magnetic Properties.[J]Cryst.Growth Des.2008,8,1213-1217.
[45]Goldberg,I.;Krupitsky,H.;Stein,Z.;Hsiou,Y.;Strouse,C.E.[J]Supramolecular Chemistry 1994,4,203-209.
[46]Balaban.T.S.;Eichh(o|¨)fer,A.;Lehn,J.-M.Self-Assembly by Hydrogen Bonding and π-π Interactions in the Crystal of a Porphyrin π-π Attempts to Mimic Bacteriochlorophyll c.[J]Eur.J.Org.Chem.2000,4047-4057.
[47]Bonifazia,D.;Accorsic,G.;Armaroli,N.;Songb,F.;Palkarb,A.;Echegoyen.L.;Scholla,M.;Seilera,P.;Jauna,B.;Diederich,F.[J]Helvetica Chimica.Acta.2005,88,1839-1884.
[48]Bolis,V.;Maggiorini,S.;Meda,L.;D'Acapito,F.;Turnes Palomino,G.;Bordiga,S.;Lamberti,C.[J]J.Chem.Phys.2000,113,9248-9261.
[1]Elemans,J.A.A.W.;Hameren,R.van;Nolte,R.J.M.;Rowan,A.E.Molecular Materials by Self-Assembly of Porphyrins,Phthalocyanines,and Perylenes.[J]Adv.Mater.2006,18,1251-1226.
[2](a) Hartgerink,J.D.;Beniash,E.;Stupp,S.Self-Assembly and Mineralization of Peptide-Amphiphile Nanopbers I.[J]Science 2001,294,1684-1688.
(b) Kitamura,T.;Nakaso,S.;Mizoshita,N.;Tochigi,Y.;Shimomura,T.;Moriyama,M.;Ito,K.;Kato,T.Electroactive Supramolecular Self-Assembled Fibers Comprised of Doped Tetrathiafulvalene-Based Gelators.[J]J.Am.Chem.Soc.2005,127,14769-14775.
[3]Schwab,A.D.;Smith,D.E.;Bond-Watts,B.;Johnston,D.E.;Hone,J.;Johnson,A.T.;de Paula,J.C.;Smith,W.F.Photoconductivity of Self-Assembled Porphyrin Nanorods.[J]Nano.Lett.2004,4,1261-1265.
[4]Wang,Z.;Li,Z.;Medforth,C.J.;Shelnutt,J.A.Self-Assembly and Self-Metallization of Porphyrin Nanosheets.[J]J.Am.Chem.Soc.2007,129,2440-2441.
[5](a) Yan,D.Y.;Zhou,Y.F.;Hou,J.Supramolecular Self-Assembly of Macroscopic Tubes.[J]Science 2004,303,65-67.
(b) Shimizu,T.;Masuda,M.;Minamikawa,H.Supramolecular Nanotube Architectures Based on Amphiphilic Molecules.[J]Chem.Rev.2005,105,1401-1444.
(c) Zhi,L.;Gorelik,T.;Wu,J.;Kolb,U.;M(u|¨)llen,K.Nanotubes Fabricated from Ni-Naphthalocyanine by a Template Method.[J]J.Am.Chem.Soc.2005,127,12792-12793.
(d) Hu,J.-S.;Guo,Y.-G.;Liang,H.-P.;Wan,L.-J.;Jiang,L.Three-Dimensional Self-Organization of Supramolecular Self-Assembled Porphyrin Hollow Hexagonal Nanoprisms[J]J.Am.Chem.Soc.2005,127,17090-17095.
[6]Liu,R.;Holman,M.W.;Zang,L.;Adams,D.M.Single-Molecule Spectroscopy of Intramolecular Electron Transfer in Donor-Bridge-Acceptor Systems.[J]J.Phys.Chem.A.2003,107,6522-6526.
[7]Holman,M.W.;Liu,R.;Zang,L.;Yan,P.;DiBenedetto,S.A.;Bowers,R.D.;Adams,D.M.Studying and Switching Electron Transfer:From the Ensemble to the Single Molecule.[J]J.Am.Chem.Soc.2004,126,16126-16133.
[8]Sauer,M.Single-Molecule-Sensitive Fluorescent Sensors Based on Photoinduced Intramolecular Charge Transfer.[J]Angew.Chem.,Int.Ed.2003,42,1790-1793.
[9]Grimsdale,A.C.;M(u|¨)llen,K.The Chemistry of Organic Nanomaterials.[J]Angew.Chem.Int.Ed.2005,44,5592-5629.
[10]Xu,B.Q.;Xiao,X.;Yang,X.;Zang,L.;Tao,N.J.Large Gate Modulation in the Current of a Room Temperature Single Molecule Transistor.[J]J.Am.Chem.Soc.2005,127,2386-2387.
[11]Li,X.;Xu,B.Q.;Xiao,X.;Yang,X.;Zang,L.;Tao,N.J.Controlling charge transport in single molecules using electrochemical gate.[J]Faraday Discuss.2006,131,111-120.
[12](a) Chen,Y.;Su,W.;Bai,M.;Jiang,J.;Li,X.;Liu,Y.;Wang,L.;Wang,S.High Performance Organic Field-Effect Transistors Based on Amphiphilic Tris(phthalocyaninato) Rare Earth Triple-Decker Complexes.[J]J.Am.Chem.Soc.2005,127,15700-15701.
(b) Li,R.;Ma,P.;Dong,S.;Zhang,X.;Chen,Y.;Li,X.;Jiang,J.Synthesis,Characterization,and OFET Properties of Amphiphilic Heteroleptic Tris(phthalocyaninato) Europium(Ⅲ) Complexes with Hydrophilic Poly(oxyethylene)Substituents.[J]Inorg.Chem.2007,46,11397-11404.
[13]Schmidt-Mende,L.;Fechtenk(o|¨)tter,A.;M(u|¨)llen,K.;Moons,E.;Friend,R.H.;MacKenzie,J.D.Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics.[J]Science 2001,293,1119-1122.
[14]Gregg,B.A.Excitonic Solar Cells.[J]J.Phys.Chem.B.2003,107,4688-4698.
[15]Gregg,B.A.Evolution of Photophysical and Photovoltaic Properties of Perylene Bis(phenethylimide) Films upon Solvent Vapor Annealing.[J]J.Phys.Chem.1996,100,852-859.
[16]Tamizhmani,G.;Dodelet,J.P.;Cote,R.;Gravel,D.Photoelectrochemical Characterization of Thin Films of Perylenetetracarboxylic Acid Derivatives[J]Chem.Mater.1991,3,1046-1053.
[17]Liu,Y.;Xiao,S.;Li,H.;Li,Y.;Liu,H.;Lu,F.;Zhuang,J.;Zhu,D.Self-Assembly and Characterization of A Novel Hydrogen-Bonded Nanostructure.[J]J.Phys.Chem.B.2004,108,6256-6260.
[18]Peeters,E.;Van Hal,P.A.;Meskers,S.C.J.;Janssen,R.A.J.;Meijer,E.W.Photoinduced Electron Transfer in a Mesogenic Donor-Acceptor-Donor System.[J]Chem.Eur.J.2002,8,4470-4474.
[19]Yokoyama,T.;Yokoyama,S.;Kamikado,T.;Yoshishige Okuno,Y.;Mashiko,T.Selective assembly on a surface of supramolecular aggregates with controlled size and shape.[J]Nature 2001,413,619-621.
[20]Balakrishnan,K.;Datar,A.;Naddo,T.;Huang,J.;Oitker,R.;Yen,M.;Zhao,J.;Zang,L.Nanobelt Self-Assembly from an Organic n-Type Semiconductor:Propoxyethyl-PTCDI.[J]J.Am.Chem.Soc.2006,128,7390-7398.
[21]Su,W.;Zhang,Y.;Zhao,C.;Li,X.;Jiang,J.Self-Assembled Organic Nanostructures:Effectof Substituents on the Morphology.[J]ChemPhysChem.2007,8,1857-1862.
[22](a) Hamza I.Intracellular Trafficking of Porphyrins.[J]ACS Chem.Biol.2006,1,627-629.
(b) Lo,P.-C.;Chan,C.M.H.;Liu,J.-Y.;Fong,W.-P.;Ng,D.K.P.Highly Photocytotoxic Glucosylated Silicon(Ⅳ) Phthalocyanines.Effects of Peripheral Chloro Substitution on the Photophysical and Photodynamic Properties[J]J.Med.Chem.2007,50,2100-2107.
(c) Vanyur,R.;Heberger,K.;Jakus,J.Prediction of Anti-HIV-1 Activity of a Series of Tetrapyrrole Molecules.[J]J.Chem.Inf.Comput.Sci.2003,43,1829-1836.
[23]Li,Y.;Li,X.;Li,Y:Liu,H.;Wang,S.;Gan,H.;Li,J.;Wang,N.;He,X.;Zhu,D.Controlled Self-Assembly Behavior of an Amphiphilic Bisporphyrin-Bipyridinium-Palladium Complex:From Multibilayer Vesiclesto Hollow Capsules.[J]Angew.Chem.Int.Ed.2006,45,3639-3643.
[24]Wang,Z.;Medforth,C.J.;Shelnutt,J.A.Porphyrin Nanotubes by Ionic Self-Assembly.[J]J.Am.Chem.Soc.2004,126,15954-15955.
[25]Shirakawa,M.;Kawano,S.-i.;Fujita,N.;Sada,K.;Shinkai S.Hydrogen-Bond-Assisted Control of H versus J Aggregation Mode of Porphyrins Stacks in an Organogel System.[J]J.Org.Chem.2003,68,5037-5044.
[26]Kimura,M.;Muto,T.;Takimoto,H.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai.H.;Kobayash,N.Fibrous Assemblies Made of Amphiphilic Metallophthalocyanines.[J]Langmuir 2000,16,2078-2082.
[27]Engelkamp,H.;Middelbeek,S.;Nolte,R.J.M.Science Magazine Search Results.[J]Science 1999,284,785-788.
[28]See for example(a) Jiang,J.;Ng,D.K.P.A Decade Journey in the Chemistry of Sandwich-Type Tetrapyrrolato Rare Earth Complexes.[J]Acc.Chem.Res.2009,42,79-88.
(b) Jiang,J.;Bao,M.;Rintoul,L.;Arnold,D.P.Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes.[J]Coord.Chem.Rev.2006,250,424-448.
(c) Jiang, J.;Kasuga,K.;Arnold,D.P.In Supramolecular Photosensitive and Electroactive Materials;[M]Nalwa,H.S.,Ed.;Academic Press:New York,2001;Chapter 2,pp 113-210.
(d) Ng,D.K.P.;Jiang,J.Sandwich-Type Heteroleptic Phthalocyaninato and Porphyrinato Metal Complexes.[J]Chem.Soc.Rev.1997,26,433-442.
(e) Yoshimoto,S.;Sawaguchi,T.;Su,W.;Jiang,J.;Kobayashi,N.Superstructure Formation and Rearrangement in the Adlayer of a Rare-Earth-Metal Triple-Decker Sandwich Complex at the Electrochemical Interface.[J]Angew.Chem.Int.Ed 2007,46,1071-1074.
(f) Ye,T.;Takami,T.;Wang,R.;Jiang,J.;Weiss,P.S.Tuning Interactions between Ligands in Self-Assembled Double-Decker Phthalocyanine Arrays[J]J.Am.Chem.Soc.2006,128,10984-10985.
[29]Liu,Q.;Li,Y.;Liu,H.;Chen,Y.;Wang,X.;Zhang,Y.;Li,X.;Jiang,J.Nanotubes Fabricated from Sandwich-Type Mixed(Porphryinato)(phthalocyaninato)europium Complex by Template Technique.[J]J.Phys.Chem.C.2007,111,7298-7301.
[30](a) Kirin,I.S.;Moskalev,P.N.;Makashev,Y.A.[J]Russ.J.Inorg.Chem.1965,10,1065-1066.
(b) Buchler,J.W.;Ng,D.K.P.In The Porphyrin Handbook;Kadish,K.M.,Smith,K.M.,Guilard,R.,Eds.;[M]Academic Press:San Diego,2000,Vol.3,pp 245-294.
(c) Sun,X.;Cui,X.;Arnold,D.P.;Choi,M.T.M.;Ng,D.K.P.;Jiang,J.The Electronic Absorption Characteristics of Mixed Phthalocyaninato Porphyrinato Rare Earth(Ⅲ) Triple-Deckers M2(TPyP)2(Pc).[J]Eur.J.Inorg.Chem.2003,8,1555-1561.
(d) Sun,X.;Li,R.;Wang,D.;Dou,J.;Zhu,P.;Lu,F.;Ma,C.;Choi,Ch-F.;Cheng,D.Y.Y.;Ng,D.K.P.;Kobayashi,N.;Jiang,J.Synthesis and Characterization of Mixed Phthalocyaninato and meso-Tetrakis(4-chlorophenyl)porphyrinato Triple-Decker Complexes-Revealing the Origin of Their Electronic Absorptions.[J]Eur.J.Inorg.Chem.2004,19,3806-3813.
[31]Kasha,M.;Rawls,H.R.;EI-Bayoumi,M.A.[J]Pure Appl.Chem.1965,11,371-392.
[32]Kimura,M.;Kuroda,T.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Self-Organization of Hydrogen-Bonded Optically Active Phthalocyanine Dimers.[J]Langmuir 2003,19,4825-4830.
[33]Minch,B.A.;Xia,W.;Donley,C.L.;Hernandez,R.M.;Carter,C.;Carducci,M.D.;Dawson,A.;O'Brien,D.F.;Armstrong,N.R.Octakis(2-benzyloxyethylsulfanyl) Copper (Ⅱ) Phthalocyanine:A New Liquid Crystalline Discotic Material with Benzyl-Terminated,Thioether-Linked Side Chains.[J]Chem.Mater.2005,17,1618-1627.
[34]Belarbi,Z.;Sidin,C.;Simon,J.;Andre,J.J.[J]J.Phys.Chem.1989,93,8105-8110.
[35]Kimura,M.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Organic-Inorganic Composites Comprised of Ordered Stacks of Amphiphilic Molecular Disks.[J]J.Am.Chem.Soc.2001,123,2438-2439.
[36]Kobayashi,T;Isoda,S.Lattice images and molecular images of organic materials.[J]J.Mater.Chem.1993,3,1-14.
[37](a) Petritsch,K.;Friend,R.H.;Lux,A.;Rozenberg,G.G.;Moratti,S.C.;Holmes,A.B.Liquid crystalline phthalocyanines in organic solar cells.[J]Synth.Met.1999,102,1776-1777.
(b) Handbook of Liquid Crystals;Demus,D.;Goodby,J.;Gray,G.W.;Spiess,H.-W.,Eds.;[M]Wiley-VCH:New York,1998;Vol.1:Fundamentals.
[38]Hoeben,F.J.M.;Jonkheijm,P.;Meijer,E.W.;Schenning,A.P.H.J.About Supramolecular Assemblies of x-Conjugated Systems.[J]Chem.Rev.2005,105,1491-1546.
[39]Babel,A.;Jenekhe,S.A.High Electron Mobility in Ladder Polymer Field-Effect Transistors.[J]J.Am.Chem.Soc.2005,125,13656-13657.
[40]Bian,Y.;Jiang,J.;Tao,Y.;Choi,M.T.M.;Li,R.;Ng,A.C.H.;Zhu,P.;Pan,N.;Sun,X.;Arnold,D.P.;Zhou,Z.;Li,H.-W.;Mak,T.C.W.;Ng,D.P.K.[J]J.Am.Chem.Soc.2003,125,12257-12267.
[41]Little,R.G.[J]J.Heter.Chem.1978,15,203-208.
[42]Littler,B.J.;Ciringh,Y.;Lindsey,J.S.Investigation of Conditions Giving Minimal Scrambling in the Synthesis of trans-Porphyrins from Dipyrromethanes and Aldehydes.[J]J.Org.Chem.1999,64,2864-2872.
[43]Stites,J.G.;McCarty,C.N.;Quill,L.L.The Rare Earth Metals and their Compounds.Ⅷ.An Improved Method for the Synthesis of Some Rare Earth Acetylacetonates.[J]J.Am.Chem.Soc.1948,70,3142-3143.
[44]Jiang,J.;Liu,R.C.W.;Mak,T.C.W.;Chan,T.W.D.;Ng,D.K.P.Synthesis,spectroscopic and electrochemical properties of substituted bis(phthalocyaninato)lanthanide(Ⅲ) complexes.[J]Polyhedron 1997,16,515-520.
[45]Gong,X.;Milic,T.;Xu,C.;Batteas,J.D.;Drain,C.M.Preparation and Characterization of Porphyrin Nanoparticles.[J]J.Am.Chem.Soc.2002,124,14290-12491.
[1][1a]J.Jiang,K.Kasuga,D.P.Arnold in Supramolecular Photo-sensitive and Electro-active Materials(Ed.:H.S.Nalwa),[M]Academic Press,New York,2001,pp.113-210.
[1b]D.K.P.Ng,J.Jiang,K.Kasuga,K.Machida in Handbook on the Physics and Chemistry of Rare Earths(Ed.:K.A.Gschneidner,Jr.,L.Eyring,G.H.Lander),[M]Elsevier,Amsterdam,2001,pp.611-654.
[1c]R.Weiss,J.Fischer in The Porphyrin Handbook,Vol.16(Eds.:K.M.Kadish,K.M.Smith,R.Guilard),[M]Academic Press,San Diego,2003,pp.172-246.
[1d]y.Chen,W.Su,M.Bai,J.Jiang,X.Li,Y.Liu,L.Wang,S.Wang,High Performance Organic Field-Effect Transistors Based on Amphiphilic Tris(phthalocyaninato) Rare Earth Triple-Decker Complexes.[J]J.Am.Chem.Soc.2005,127,15700-15701.
[2]J.Jiang,W.Liu,D.P.Arnold,Sandwich complexes of naphthalocyanine with the rare earth metals.[J]J.Porphyrins Phthalocyanines 2003,7,459-473.
[3]D.K.P.Ng,J.Jiang,Sandwich-type heteroleptic phthalocyaninato and porphyrinato metal complexes.[J]Chem.Soc.Rev.1997,26,433-442.
[4][4a]K.H.Yew,H.J.Koh,H.W.Lee,I.Lee,[J]J.Chem.Soc.,Perkin Trans.2 1995,2263-2268.
[4b]T.Itoh,R.Noki,S.Simosato,I.Magara,S.Iwatsuki,[J]J.Polymer Science,Part A:Polymer Chemistry 1995,33,1475-1485.
[5]U.Diefenbach,H.R.Allcock,Synthesis of Cyclo- and Polyphosphazenes with Pyridine Side Groups.[J]Inorg.Chem.1994,33,4562-4565.
[6]R.Li,X.Zhang,P.Zhu,D.K.P.Ng,N.Kobayashi,J.Jiang,Electron-Donating or -Withdrawing Nature of Substituents Revealed by the Electrochemistry of Metal-Free Phthalocyanines.[J]Inorg.Chem.2006,45,2327-2334.
[7]A.Pondaven,Y.Cozien,M.L'Her,[J]New.J.Chem.1991,15,515-516.
[8]A.Pondaven,Y.Cozien,M.L'Her,[J]New.J.Chem.1992,16,711-718.
[9][9a]F.Guyon,A.Pondaven,P.Guenot,M.L'Her,Bis(2,3-naphthalocyaninato)lutetium(Ⅲ) and (2,3-Naphthalocyaninato)(phthalocyaninato)lutetium(Ⅲ) Complexes:Synthesis,Spectroscopic Characterization,and Electrochemistry.[J]Inorg.Chem.1994,33,4787-4793.
[9b]C.Cadiou,A.Pondaven,M.L'Her,P.Jehan,P.Guenoy,An Amphiphilic Lutetium Bisphthalocyanine:Lu[(PEO)4Pc][(DodO)4Pc][J]J.Org.Chem.1999,64, 9046-9050.
[9c]L.Gaimiche,F.Guyon,A.Pondaven,J.-Y.Moisan,M.L'Her.Photogeneration of charges in poly(N-vinylcarbazole) doped with lutetium bisphthalocyanines and lutetium bisnaphthalocyanines.[J]J.Porphyrins and Phthalocyanines 2003,7,382-387.
[10][10a]J.Jiang,W.Liu,W.Law,J.Lin,D.P.Arnold,A new synthetic route to unsymmetrical bis(phthalocyaninato)europium(Ⅲ) complexes.[J]Inorg.Chem.Acta 1998,268,141-144.
[10b]J.Jiang,J.Xie,M.T.M.Choi,D.K.P.Ng,Double-decker yttrium(Ⅲ) complexes with phthalocyaninato and porphyrinato ligands.[J]J.Porphyrins Phthalocyanines 1999,3,322-328.
[10c]Y.Bian,R.Wang,J.Jiang,C.-H.Lee,J.Wang and D.K.P.Ng,Synthesis,spectroscopic characterisation and structure of the first chiral heteroleptic bis(phthalocyaninato) rare earth complexes.[J]Chem.Commun.2003,1194-1195.
[10d]J.Jiang,R.C.W.Liu,T.C.W.Mak,T.W.D.Chan,D.K.P.Ng,Synthesis,spectroscopic and electrochemical properties of substituted bis(phthalocyaninato)lanthanide(Ⅲ) complexes.[J]Polyhedron 1997,16,515-520.
[11][11a]J.Jiang,D.P.Arnold,H.Yu,Infra-red spectra of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes[J]Polyhedron 1999,18,2129-2139.
[11b]X.Sun,M Bao,N.Pan,X Cui,D.P.Arnold,J.Jiang,[J]Aust.J.Chem.2002,9,587-595.
[11c]F.Lu,M.Bao,C.Ma,X.Zhang,D.P.Arnold,J.Jiang,[J]Spectrochim Acta Part A 2003,59,3273-3286.
[11d]M.Bao,N.Pan,C.Ma,D.P.Arnold,J.Jiang,Infrared spectra of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes:Part 4.The infrared characteristics of phthalocyanine in heteroleptic tris(phthalocyaninato) rare earth complexes.[J]Vibrational Spectroscopy 2003,32,175-184.
[11e]M.Bao,Y.Bian,L.Rintoul,R.Wang,D.P.Arnold,C.Ma,J.Jiang,Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type (na)phthalocyaninato and porphyrinato rare earth complexes:(Part 10) The infrared and Raman characteristics of phthalocyanine in heteroleptic bis(phthalocyaninato) rare earth complexes with decreased molecular symmetry[J]Vibrational Spectroscopy 2004,34,283-291.
[11f]J.Jiang,M.L.Rintoul,D.P.Arnold,Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes.[J]Coord.Chem.Rev.2006,250,424-448.
[12]Y.Bian,J.Jiang,Y.Tao,M.T.M.Choi,R.Li,A.C.H.Ng,P.Zhu,N.Pan,X.Sun,D.P. Arnold,Z.Zhou,H.-W.Li,D.K.P.Ng,Tuning the Valence of the Cerium Center in (Na)phthalocyaninato and Porphyrinato Cerium Double-Deckers by Changing the Nature of the Tetrapyrrole Ligands.[J]J.Am.Chem.Soc.2003,125,12257-12267.
[13]J.Jiang,Y Bian,F.Furuya,W.Liu,M.T.M.Choi,N.Kobayashi,H.-W.Li,Q.Yang,T.C.W.Male,D.K.P.Ng,Synthesis,Structure,Spectroscopic Properties,and Electrochemistry of Rare Earth Sandwich Compounds with Mixed 2,3-Naphthalocyaninato and Octaethylporphyrinato Ligands.[J]Chem.Eur.J.2001,7,5059-5069.
[14]J.Jiang,W.Liu,K.-L.Cheng,K.-W.Poon,D.K.P.Ng,Heteroleptic Rare Earth Double-Decker Complexes with Porphyrinato and 2,3-Naphthalocyaninato Ligands-Preparation,Spectroscopic Characterization,and Electrochemical Studies.[J]Eur.J.Inorg.Chem.2001,413-417.
[15]F.Lu,X.Sun,R.Li,D.Liang,P.Zhu,X.Zhang,C.-F.Choi,D.K.P.Ng,T.Fukuda,N.Kobayashi,J.Jiang,Synthesis,spectroscopic properties,and electrochemistry of heteroleptic rare earth double-decker complexes with phthalocyaninato and meso-tetrakis(4-chlorophenyl)porphyrinato ligands.[J]New J.Chem.2004,28,1116-1122.
[16]P.Zhu,F.Lu,N.Pan,D.P.Arnold,S.Zhang,J.Jiang,J.Comparative Electrochemical Study of Unsubstituted and Substituted Bis(phthalocyaninato) Rare Earth(Ⅲ)Complexes.[J]Eur.J.Inorg.Chem.2004,510-517.
[17]~([17a]) E.Orti,J.L.Bredas,[J]J.Chem.Phys 1990,92,1228-1235.
~([17b]) N.Ishikawa,Electronic structures and spectral properties of double-and triple-decker phthalocyanine complexes in a localized molecular orbital view.[J]J.Porphyrins Phthalocyanines 2001,5,87-101.
[18]J.G.Stites,C.N.McCarty,L.L.Quill,The Rare Earth Metals and their Compounds.Ⅷ.An Improved Method for the Synthesis of Some Rare Earth Acetylacetonates.[J]J.Am.Chem.Soc.1948,70,3142-3143.
[19]D.Wohrle,M.Eskes,K.Shigehara,A.Yamada,[J]Synthesis 1993,194-196.
[20]~([20a]) J.J.p.Stewart,[J]J.Comp.Chem.1989,10,209-220.
~([20b]) J.J.p.Stewart,[J]J.Comp.Chem.1989,10,221-264.
[21]X.Zhang,Y.Zhang,J.Jiang,[J]J.Mol.Struct.THEOCHEM,,2004,673,103-108.
[22]M.J.Frisch et al.,Gaussian-98,Revision A.9,Gaussian,Inc.,Pittsburgh PA,1998.
[23] SMART and SAINT for Windows NT Software Reference Manuals, [M] Version 5.0, Bruker Analytical X-Ray Systems, Madison, WI, 1997.
[24] G. M. Sheldrick, SADABS - A Software for Empirical Absorption Correction, [M] University of Gottingen, 1997.
[25] SHELXL Reference Manual, [M] Version 5.1, Bruker Analytical X-Ray Systems, Madison, WI, 1997.
[1]~([1a]) J.Jiang,K.Kasuga,D.P.Arnold in Supramolecular Photo-sensitive and Electro-active Materials(Ed.:H.S.Nalwa),Academic Press,New York,2001,pp.113-210.
~([1b]) D.K.P.Ng,J.Jiang,K.Kasuga,K.Machida in Handbook on the Physics and Chemistry of Rare Earths(Ed.:K.A.Gschneidner,Jr.,L.Eyring,G.H.Lander),Elsevier,Amsterdam,2001,pp.611-654.
~([1c]) R.Weiss,J.Fischer in The Porphyrin Handbook,Vol.16(Eds.:K.M.Kadish,K.M.Smith,R.Guilard),Academic Press,San Diego,2003,pp.172-246.
~([1d]) y.Chen,W.Su,M.Bai,J.Jiang,X.Li,Y.Liu,L.Wang,S.Wang,J.Am.Chem.Soc.2005,127,15700-15701.
[2]J.Jiang,W.Liu,D.P.Arnold,J.Porphyrins Phthalocyanines 2003,7,459-473.
[3]D.K.P.Ng,J.Jiang,Chem.Soc.Rev.1997,26,433-442.
[4]~([4a]) K.H.Yew,H.J.Koh,H.W.Lee,I.Lee,J.Chem.Soc.,Perkin Trans.2 1995,2263-2268.
~([4b]) T.Itoh,R.Noki,S.Simosato,I.Magara,S.Iwatsuki,J.Polymer Science,Part A:Polymer Chemistry 1995,33,1475-1485.
[5]U.Diefenbach,H.R.Allcock,Inorg.Chem.1994,33,4562-4565.
[6]R.Li,X.Zhang,P.Zhu,D.K.P.Ng,N.Kobayashi,J.Jiang,Inorg.Chem.2006,45,2327-2334.
[7]A.Pondaven,Y.Cozien,M.L'Her,New.J.Chem.1991,15,515-516.
[8]A.Pondaven,Y.Cozien,M.L'Her,New.J.Chem.1992,16,711-718.
[9]
~([9a]) F.Guyon,A.Pondaven,P.Guenot,M.L'Her,Inorg.Chem.1994,33,4787-4793.
~([9b])C.Cadiou,A.Pondaven,M.L'Her,P.Jehan,P.Guenoy,J.Org.Chem.1999,64,9046-9050.
~([9c]) L.Gaimiche,F.Guyon,A.Pondaven,J.-Y.Moisan,M.L'Her.J.Porphyrins and Phthalocyanines 2003,7,382-387.
[10]~([10a]) J.Jiang,W.Liu,W.Law,J.Lin,D.P.Arnold,Inorg.Chem.Acta 1998,268,141-144.
~([10b]) J.Jiang,J.Xie,M.T.M.Choi,D.K.P.Ng,J.Porphyrins Phthalocyanines 1999,3,322-328.
~([10c]) y.Bian,R.Wang,J.Jiang,C.-H.Lee,J.Wang and D.K.P.Ng,Chem.Commun.2003,1194-1195.
~([10d]) J.Jiang,R.C.W.Liu,T.C.W.Mak,T.W.D.Chan,D.K.P.Ng,Polyhedron 1997,16,515-520.
[11]~([11a]) J.Jiang,D.P.Arnold,H.Yu,Polyhedron 1999,18,2129-2139.
~([11b]) X.Sun,M Bao,N.Pan,X Cui,D.P.Arnold,J.Jiang,Aust.J.Chem.2002,9,587-595.
~([11c]) F.Lu,M.Bao,C.Ma,X.Zhang,D.P.Arnold,J.Jiang,Spectrochim Acta Part A 2003,59,3273-3286.
~([11d]) M.Bao,N.Pan,C.Ma,D.P.Arnold,J.Bang,Vibrational Spectroscopy 2003,32,175-184.
~[11e]) M.Bao,Y.Bian,L.Rintoul,R.Wang,D.P.Arnold,C.Ma,J.Jiang,Vibrational Spectroscopy 2004,34,283-291.
~([11f]) J.Jiang,M.L.Rintoul,D.P.Arnold,Coord.Chem.Rev.2006,250,424-448.
[12]Y.Bian,J.Jiang,Y.Tao,M.T.M.Choi,R.Li,A.C.H.Ng,P.Zhu,N.Pan,X.Sun,D.P.Arnold,Z.Zhou,H.-W.Li,D.K.P.Ng,J.Am.Chem.Soc.2003,125,12257-12267.
[13]J.Jiang,Y.Bian,F.Furuya,W.Liu,M.T.M.Choi,N.Kobayashi,H.-W.Li,Q.Yang,T.C.W.Mak,D.K.P.Ng,Chem.Eur.J.2001,7,5059-5069.
[14]J.Jiang,W.Liu,K.-L.Cheng,K.-W.Poon,D.K.P.Ng,Eur.J.Inorg.Chem.2001,413-417.
[15]F.Lu,X.Sun,R.Li,D.Liang,P.Zhu,X.Zhang,C.-F.Choi,D.K.P.Ng,T.Fukuda,N. Kobayashi,J.Jiang,New J.Chem.2004,28,1116-1122.
[16]P.Zhu,F.Lu,N.Pan,D.P.Arnold,S.Zhang,J.Jiang,J.Eur.J.Inorg.Chem.2004,510-517.
[17]~([17a]) E.Orti,J.L.Bredas,J.Chem.Phys.1990,92,1228-1235.
[17b]N.Ishikawa,J.Porphyrins Phthalocyanines 2001,5,87-101.
[18]J.G.Stites,C.N.McCarty,L.L.Quill,J.Am.Chem.Soc.1948,70,3142-3143.
[19]D.Wohrle,M.Eskes,K.Shigehara,A.Yamada,Synthesis 1993,194-196.
[20]~([20a]) J.J.P.Stewart,J.Comp.Chem.1989,10,209-220.
~([20b]) J.J.p.Stewart,J.Comp.Chem.1989,10,221-264.
[21]X.Zhang,Y.Zhang,J.Jiang,J.Mol.Struct.THEOCHEM,,2004,673,103-108.
[22]M.J.Frisch et al.,Gaussian-98,Revision A.9,Gaussian,Inc.,Pittsburgh PA,1998.
[23]SMART and SAINT for Windows NT Software Reference Manuals,Version 5.0,Bruker Analytical X-Ray Systems,Madison,WI,1997.
[24]G.M.Sheldrick,SADABS-A Software for Empirical Absorption Correction,University of G(o|¨)ttingen,1997.
[25]SHELXL Reference Manual,Version 5.1,Bruker Analytical X-Ray Systems,Madison,WI,1997.
[2]J.Zelaski.Porphyrin[J]Z.Physiol.Chem.,1902,37,54.
[3]C.P.Wang et al.Lanthanide porphyrin complexes.Potential new class of nuclear magnetic resonance dipolar probe.[J]J.Am.Chem.Soc.,1974,96,7149-7150.
[4]C.P.Wang et al.Porphyrin complexes.[J]Tetrahydron Lett.,1975,31,237.
[5]计亮年,彭小彬,黄锦汪.金属卟啉配合物模拟某些金属酶的研究进展自然科学进展[J]2002,12,120-129.
[6]J.S.Sessler,S.J.Weghom.Expended,Contracted,81 isomeric porphyrins[M]Pergamon,Perface,1997.
[7]李德平,胡静.血卟啉类化合物诊治肿瘤的研究进展及应用[J]中国生化药物杂志,2003,24,162-163.
[8]杨新国,孙景志,汪茫,陈红征,黄骥.卟啉类光电功能材料研究进展[J]功能材料,2003,34,113-117.
[9](a) N.Uyeda,T.Kobayashi,E.Suito,Y.Harada,M.Watanabe.Molecular image resolution in electron microscopy[J]J.Appl.Phys.,1972,43,5181-5189.
(b) T.Kobayashi,S.Isoda.Lattice Images and Molecular Images of Organic Materials[J]J.Mater.Chem.1993,3,1-14.
[10]Eley,D.D.Phthalocyanines as semiconductors[J]Nature 1948,162,819-819.
[11](a) Schramm,C.J.,Stojakovic,D.R.,Hoffman,B.M.&Marks,T.J.;New low-dimensional molecular metals:single-crystal electrical conductivity of nickel phthalocyanine iodide[J]Science,1978,200,47.
(b) Marks,T.J.,Electrically conductive metallomacrocyclic assemblies;[J]Science,1985,227,881-889.
[12](a) Bott,B.,Jones,T.A.;A highly sensitive NO_2 sensor based on electrical conductivity changes in phthalocyanine films;[J]Sensors&Actuators,1984,5,43.
(b)Wright,J.D.;Gas adsorption on phthalocyanines and its effects on electrical properties.[J]Prog.Surf.Sci.1989,31,1.
[13]Vartanyan,A.T.Poluprovodnikovye Svoistva Organicheskikh Krasitel[J]Zh.Fiz Khim.948,22,769-774.
[14]Law,K.-Y.Organic photoconductive materials:recent trends and developments.[J]Chem.Rev.,1993,93,449-486
[15]Tang,C.W.;Two-layer organic photovoltaic cell;[J]Appl.Phys.Lett.,1986,48,183-185
[16]Nazeeruddin,M.K.,et al,Efficient near IR sensitization of nanocrystalline TiO_2films by ruthenium phthalocyanines.[J]Chem.Commun.,1998,719-720
[17]Wohrle,D.,et al,Microlasers based on organic dyes in nanoporous crystals[J]Molecular Crystals&Liquid Crystals,1993,230,221.
[18]王朝晖,衷庆华,熊轶嘉,孙亚,孔繁敖.酞菁锌分子激发态的超快内转换和振动弛豫[J]化学物理学报,1998,2,15-18.
[19]De la Torre,G,Vazquez.P.et al.Phthalocyanines and related compounds.[J]J.Mater Chem.,1998,8,1671-1683.
[20]Shirk J.S.,Lindle J.R.,Bartoli F.J.et al.Third-order optical nonlinearities of bis(phthalocyanines)[J]J.Phys.Chem.,1992,96,5847-5852.
[21]陈仕艳,刘云圻,黄学斌,邱文丰,朱道本.酞菁在分子材料器件方面的研究进展[J]自然科学进展,2004,14,125-132.
[22]C.C.Leznoff,A.B.P.Lever.Phthalocynines:properties and applications.[M]Volumes 1-4,New York:VCH,1989.
[23]Borisenkova,S.A.New aspects of the heterogeneous catalysis of thiol oxidation by phthalocyanines.[J]Petroleum Chem.1991,31,379-398.
[24]Bennett W.E.,Broberg D.E.,Baenziger N.C.Crystal structure of stannic phthalocyanine,an eight-coordinated tin complex[J]Inorg.Chem.1973,12,930-936.
[25]Kirin I.S.,Moskalev E N.,Makashev Yu.A.Formation of phthalocyanines of rare-earth elements[J]Russ.J.Inorg.Chem.1965,10,1065.
[26]Cian A.De.,Moussavi M.,Fischer J.et al.,Synthesis,structure,and spectroscopic and magnetic properties of lutetium(Ⅲ) phthalocyanine derivatives[J]Inorg.Chem.,1985,24,3162-3167.
[27](a) Lux F.,Dempf D.,Graw D.,Diphthalocyaninato-thorium(Ⅳ) and-uranium(Ⅳ)[J]Angew.Chem.Int.Ed.Eng.,1968,7,819-820.
(b) Lux,F.,Brwon,D.,Dempf,D.et al.Synthesis of 1-Adamantanecarbaldehydes.[J]Angew.Chem.Int.Ed.Eng.1969,7,894.
[28]M.Bouvet,J.Smion,Electrical properties of rare earth bisphthalocyanine and bisnaphthalocyanine complexes.[J]Chem.Phys.Lett.1990,172,299
[29]D.K.P.Ng,J.Jiang.,Sandwich-Type Heteroleptic Phthalocyaninato and Porphyrinato Metal Complexes[J]Chem.Soc.Rev.1997,26,433-442.
[30]姜建壮,吴基培,刘伟,谢经雷,孙思修.对称的二层及三层三明治型金属酞菁配合物的研究进展.[J]化学通报.1999,2.
[31]A.Gieren,W.Hoppe,X-Ray crystal structure analysis of bisphthalocy aninatouranium[J]Chem.Commun.1971,413.
[32]Cian.A.De;Moussavi M;Fischer J;et al.;Synthesis,structure,and spectroscopic and magnetic properties of lutetium(Ⅲ) phthalocyanine derivatives[J]Inorg.Chem.1985,24,3162.
[33]Koike.N.,Uekusa.H.,Ohashi Y.;et al.;Relationship between the Skew Angle and Interplanar Distance in Four Bis(phthalocyaninato)lanthanide(Ⅲ) Tetrabutyl ammonium Salts([NBun_4][LnPc_2];Ln=Nd,Gd,Ho,Lu)[J]Inorg.Chem.1996,35,5798.
[34]J.Buchler,A.D.C.J.Fischer;M.K.Botulinski;H.Paulus;R.Weiss.;Metal complexes with tetrapyrrole ligands.Cerium(Ⅳ) bis-(octaethylporphyrinate) and dicerium(Ⅲ) tris(oetaethylporphyrinate):Parents of a new family of lanthanoid double-decker and triple-decker molecules;[J]J.Am.Soc.1986,108;3652.
[35]G.C.S.Collins;D.J.Schiffrin;The electrochromic properties of lutetium and other phthalocyanines.[J]J.Electroanal.Chem.1982,139,335.
[36]C.S.Frampton;J.M.O'Connor;J.Peterson;J.Silver,Enhanced colors and properties in the electrochromic behavior of mixed rare-earth-element bisphthalcoyanines.[J]Displays,1988,9,174.
[37]A.Capobianchi,A.M.Paoletti,G.Pennesi,G.Rossiand S.Paner;Electrochromism in sandwich-type diphthalocyanines:electrochemical and spectroscopic behaviour of bis(phthalocyaninato)titanium(Ⅳ)(Ti(Pc)_2) film.[J]Synth.Met.1995,75,37.
[38]McKeown,N.B.;The general chemistry of phthalcoyanines.[J]Chem.& Industry;1999,Feb.1,92.
[39]J.J.Andre,K.Holczer,P.Petit,M.T.Riou,J.Smon;Electrical and magnetic properties of thin films and single crystals of bis(phthalocyaninato) lutetium.[J]Chem.Phys.Lett.1985,115,463.
[40]J.Padilla and W.E.Hatifield.Magnetic and electrical properties of sandwich-like lanthanide phthalocyanines;[J]Synth.Met.1989,29,F45.
[41]J.Padilla and W.E.Hatifield;Correlation between π-orbital overlap and conductivity in bis-phthalocyaninato lanthanides;[J]Inorg.Chim.Acta.1991,185.131.
[42]J.Souto,R.Aroca,J.A.Desaja;Gas Adsorption and Electrical Conductivity of Langrnuir-Blodgett Films of Terbium Bisphthalocyanine.[J]J.Phys.Chem.1994,98,8998.
[43]M.Trometer,R.Even,J.Simon,A.Dubon and J.-Y.LavalJ.P.Germain,C.Maleysson,A.Pauly and H.Robert;Lutetium bisphthalocyanine thin films for gas detection.[J]Sens.Actuators B.1992,8,129.
[44]J.Simon and S.Sidin;Mesomorphic molecular materials for electronics,optoelectronics,iono-electronics:octaalkylphthalocyanine derivatives[J]Pure Appl.Chem.1989,61,1625.
[45]G.Guillaud,M.Al Sadoun,M.Maitrot,J.J.Andre,J.Simon and R.Even.Field-effect transistors based on intrinsic molecular semiconductors[J]Chem.Phys.Lett.1988,167,503.
[46]C.Clarisse,M.T.Riou,M.Gauneau and M.Le Cntellec.Field-Effect Transistor with Diphthalocyanine Thin Film[J]Electron.Lett.1988,24,674.
[47]T.Toupance,V.Ahsen and J.Simon.Iono-electronics:crown ether substituted lutetium bisphthalocyanines[J]J.Chem.Soc.,Chem.Commun.1994,75-76.
[48]Nicholson M.M,Pizzarello F.A.The redox chemistry of phthalocyanine[J]J.Electrochem Soc,1980,127,2617.
[49]Nicholson M.M,Pizzarello F.A.;The role of oxygen in the redox chemistry of luterrium diphthalocyanine;[J]J.Electrochem Soc,1984,131,2311.
[50]K.L.Trojan,J.L.Kendall,K.D.Kepler and W.E.Hatfield;Strong exchange coupling between the lanthanide ions and the phthalocyaninato ligand radical in bis(phthalocyaninato)lanthanide sandwich compounds[J]Inorg.Chim.Acta.1992,198,795.
[51](a) Lehn J.M.Supramolecular Chemistry-Concepts and Perspectives.[M]Weinheim:VCH Publishers,1995;
(b)V(o|¨)gtle F.著.张希,林志宏,高倩译,超分子化学.[M]长春:吉林大学出版社,1995:
(c)Ringsdorf,H.;Schlarb,B.:Venzmer J.Molecular architecture and function in polymeric oriented systems:models for the study of organization,surface recognition,and dynamics in biomembranes.[J]Angew.Chem.Int.Ed.1998,27,113;
(d) Zhang,X.;Shen,J.C.self-assembled ultrathin films:from layered nanoarchitectures to functional assemblies.[J]Adv.Mater.,1999,11,1139.
[52]Vogtle,F.Supramolekulare Chemic,[M]Teubner,Stuttgart,1991.
[53](a) Cram.D.J.The Design of Molecular Hosts,Guests,and Their Complexes;[J]Angew.Chem.Int.Ed.1988,27,1009-1020.
(b) Lehn,J.-M.Supramolecular Chemistry-Scope and Perspectives Molecules,Supermolecules,and Molecular Devices;[J]Angew.Chem.Int.Ed.1988,27,89-112.
[54](a) Lehn,J.-M.Perspectives in Supramolecular Chemistry-From Molecular Recognition towards Molecular Information Processing and Self-Organization.[J]Angew.Chem.Int.Ed.1990,29,1304-1319.
(b) Lehn,J.-M.Supramolecular chemistry.[J]Science 1993,260,1762-1763.
(c) Lehn,J.-M.Supramolecular Chemistry:Concepts and Perspectives;[M]VHC,Weinheim,1995.
[55]Lehn J.M.Programmed Chemical Systems:Multiple Subprograms and Multiple Processing/Expression of Molecular Information.[J]Chem.Eur.J.,2000,6,2097-2102.
[56]吴世康编著,超分子光化学导论,[M]北京 科学出版社,2005.
[57](a) Balzani,V.;Credi,A.;Raymo,F.M.;Stoddart,J.F.Artificial Molecular Machines.[J]Angew.Chem.Int.Ed,2000,39,3348-3391.
(b) 刘育,尤长城,张衡益著 超分子化学-合成受体的分子识别与组装[M]天津 南开大学出版社,2001.
[58]刘海洋,胡希明,应晓,刘义,黄锦汪,计亮年,金属卟啉配合物超分子弹自组装.[J]无机化学学报,1998,14,371-387.
[59]Drain,C.M.,Lehn,J.M.,[J]J.Chem.Soc.Chem.Commun.,1994,2313-2314.
[60]Drain,C.M.;Nifiatis,F.;Vasenko,A.;Batteas,J.D.Porphyrin Tessellation by Design:Metal-Mediated Self-Assembly of Large Arrays and Tapes.[J]Angew.Chem.Int.Ed.,1998,37,2344-2347.
[61]Engelkamp,H.;Middelbeek,S.;Nolte,R.J.M.Self-Assembly of Disk-Shaped Molecules to Coiled-Coil Aggregates with Tunable Helicity.[J]Science,1999,284,785-788
[62](a) Shirakawa,M.;Fujita,N.;Shinkai,S.A Stable Single Piece of Unimolecularly π-Stacked Porphyrin Aggregate in a Thixotropic Low Molecular Weight Gel:A One-Dimensional Molecular Template for Polydiacetylene Wiring up to Several Tens of Micrometers in Length.[J]J.Am.Chem.Soc.2005,127,4164-4165.
(b) Kishida,T.;Fujita,N.;Sada,K.;Shinkai,S.Sol-Gel Reaction of Porphyrin-Based Superstructures in the Organogel Phase:Creation of Mechanically Reinforced Porphyrin Hybrids.[J]J.Am.Chem.Soc.2005,127,7298-7299.
(c) Shirakawa,M.;Fujita,N.;Shinkai,S.[60]Fullerene-Motivated Organogel Formation in a Porphyrin Derivative Bearing Programmed Hydrogen-Bonding Sites.[J]J.Am.Chem.Soc.2003,125,9902-9903.
(d) Sano,M.;Kamino,A.;Okamura,J.;Shinkai,S.Self-Organization of PEO-graft-Single-Walled Carbon Nanotubes in Solutions and Langmuir-Blodgett Films.[J]Langmuir,2001,17,5125-5128.
[63]Tamaru S.I.;Nakamuira,M.;Takeuchi M.;Shinkai S.Rational Design of a Sugar-Appended Porphyrin Gelator That Is Forced To Assemble into a One-Dimensional Aggregate.[J]Org.Lett.,2001,3,3631-3634.
[64]Ayabe,M.;Yamashita,K.;Shinkai,S.;Ikeda,A.;Sakamoto,S.;Yamaguchi,K.Construction of Monomeric and Polymeric Porphyrin Compartments by a Pd(Ⅱ)-Pyridine Interaction and Their Chiral Twisting by a BINAP Ligand.[J]J.Org.Chem.,2003,68,1059-1066.
[65]Hu,J.-S.;Guo,Y.-G.;Liang,H.-P.;Wan,L.-J.;Jiang,L.Three-Dimensional Self-Organization of Supramolecular Self-Assembled Porphyrin Hollow Hexagonal Nanoprisms.[J]J.Am.Chem.Soc.2005,127,17090-17095.
[66](a) Wang,Z.;Medforth,C.J.;Shelnutt,J.A.Porphyrin Nanotubes by Ionic Self-Assembly.[J]J.Am.Chem.Soc.,2004,126,15954-15955.
(b) Wang,Z.;Medforth,C.J.;Shelnutt,J.A.Self-Metallization of Photocatalytic Porphyrin Nanotubes.[J]J.Am.Chem.Soc.,2004,126,16720-16721.
[67]Gong,X.;Milic,T.;Xu,C.;Batteas,J.D.;Drain,C.M.Preparation and Characterization of Porphyrin Nanoparticles.[J]J.Am.Chem.Soc.2002,124,14290-14291.
[68](a) Kimura,M.;Muto,T.;Takimoto,H.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai.H.;Kobayash,N.Fibrous Assemblies Made of Amphiphilic Metallophthalocyanines.[J]Langmuir 2000,16,2078-2082.
(b) Kimura,M.;Kuroda,T.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Self-Organization of Hydrogen-Bonded Optically Active Phthalocyanine Dimers.[J]Langmuir 2003,19,4825-4830.
[69](a) Nitschke,C.;O'Flaherty,S.M.;Kroll,M.;Blau,W.J.Material Investigations and Optical Properties of Phthalocyanine Nanoparticles.[J]J.Phys.Chem.B.,2004,108,1287-1295.
(b) Zhang,X.;Wang,Y.;Ma,Y.;Ye,Y.;Wang,Y.;Wu,K.Solvent-Stabilized Oxovanadium Phthalocyanine Nanoparticles and Their Application in Xerographic Photoreceptors.[J]Langmuir,2006,22,344-348.
[70]K.Ishii,Y.Ohba,M.Iwaizumi and S.Yamauch,Studies on Monomers and Dimers of Y(Ⅲ) and La(Ⅲ) Porphyrin Complexes by Time-Resolved Electron Paramagnetic Resonance[J]J.Phys.Chem.1996,100,3839-3846.
[71]H.Konami,M.Hatano,N.Kobayashi and T.Osa.Redox potentials of a series of lanthanide-bisphthalocyanine sandwich complexes.[J]Chem.Phys.Lett.1990,165,397-400.
[72]J.Padilla and W.E.Hatfield,σ and π-interactions of the pyrrolillc ligand of sandwich-like lanthanide phthalocyanines determined from magnetic susceptibility and ligand-field theory.[J]Inorg.Chim.Acta,1990,172,241.
[73]E.Oriti,J.L.Bredas and C.Clarisse,Studies on Monomers and Dimers of Y(Ⅲ) and La(Ⅲ) Porphyrin Complexes by Time-Resolved Electron Paramagnetic Resonance;[J]J.Chem.Phys.1990,92,1228.
[74]P.C.Martin,J.Arnold,and D.F.Bocian;Spectroscopic characterization of zirconium (Ⅳ) and hafnium(Ⅳ) sandwich porphyrin complexes;[J]J.Phys.Chem.1993,97,1332
[75]J.W.Buchler and B.Scharbert,Metal complexes with tetrapyrrole ligands.50.Redox potentials of sandwichlike metal bis(octaethylporphyrinates) and their correlation with ring-ring distances.[J]J.Am.Chem.Soc.1988,110,4272-4278.
[76]J.Jiang,W.Liu,-F.Law,and D.K.P.Ng;A new synthetic route to unsymmetrical bis (phthalocyaninato)europium(Ⅲ) complexes.[J]Inorg.Chim.Acta,1998,268,141-144.
[1]Schouten,P.G.;Warman,J.M.;de Haas,M.P.;Fox,M.A.;.Pan,H.L.Charge migration in supramolecular stacks of peripherally substituted porphyrins.[J]Nature 1991,353,736-737.
[2]J.-M.Lehn,Toward Self-Organization and Complex Matter.[J]Science 2002,295,2400-2403.
[3]Gan,H.;Liu,H.;Li,Y.;Zhao,Q.;Li,Y.;Wang,S.;Jiu,T.;Wang,N.;He,X.;Yu,D.;Zhu,D,Fabrication of Polydiacetylene Nanowires by Associated Self-Polymerization and Self-Assembly Processes for Efficient Field Emission Properties.[J]J.Am.Soc.Chem.2005,127,12452-12453.
[4]Balakrishnan,K.;Datar,A.;Naddo,T.;Huang,J.;Oitker,R.;Yen,M.;Zhao,J.;Zang,L.Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules:Morphology Control.[J]J.Am.Chem.Soc.2006,128,7390-7398.
[5]Vriezema,D.M.;Hoogboom,J.;Velonia,K.;Takazawa,K.;Christianen,P.C.M.;Maan,J.C.;Rowan,A.E.;Nolte,R.J.M.Vesicles and Polymerized Vesicles from hiophene-Containing Rod-Coil Block Copolymers.[J]Angew.Chem.Int.Ed.2003,42,772-776.
[6](a) Yan,D.Y.;Zhou,Y.F.;Hou,J.Supramolecular Self-Assembly of Macroscopic Tubes.[J]Science 2004,303,65-67.
(b) Hu,J.-S.;Guo,Y.-G.;Liang,H.-P.;Wan,L.-J.;Jiang,L.Three-Dimensional Self-Organization of Supramolecular Self-Assembled Porphyrin Hollow Hexagonal Nanoprisms.[J]J.Am.Chem.Soc.2005,127,17090-17095.
(c) Shimizu,T.;Masuda,M.;Minamikawa,H.Supramolecular Nanotube Architectures Based on Amphiphilic Molecules.[J]Chem.Rev.2005,105,1401-1444.
(d) Zhi,L.;Gorelik,T.;Wu,J.;Kolb,U.;M(u|¨)llen,K.Nanotubes Fabricated from Ni-Naphthalocyanine by a Template Method.[J]J.Am.Chem.Soc.2005,127,12792-12793.
(e) Liu,Q.;Li,Y.;Liu,H.;Chen,Y.;Wang,X.;Zhang,Y.;Li,X.;Jiang,J.Nanotubes Fabricated from Sandwich-Type Mixed(Porphryinato)(phthalocyaninato)europium Complex by Template Technique.[J]J.Phys.Chem.C.2007,111,7298-7301.
[7]Charvet,R.;Jiang,D.L.;Aida,T.Self-assembly of a n-electronic amphiphile consisting of a zinc porphyrin-fullerene dyad:formation of micro-vesicles with a high stability.[J]Chem.Commun.2004,2664-2665.
[8]Li,Y.;Li,X.;Li,Y:Liu,H.;Wang,S.;Gan,H.;Li,J.;Wang,N.;He,X.;Zhu,D.Controlled Self-Assembly Behavior of an Amphiphilic Bisporphyrin-Bipyridinium-Palladium Complex:From Multibilayer Vesicles to Hollow Capsules.[J]Angew.Chem.Int.Ed.2006,45,3639-3643.
[9](a) Zupan,K.;Herenyi,L.;Toth,K.;Majer,Z.;Csik,G.Binding of Cationic Porphyrin to Isolated and Encapsidated Viral DNA Analyzed by Comprehensive Spectroscopic Methods.[J]Biochemistry,2004,43,9151-9159.
(b) Zupan,K.;Herenyi,L.;Toth,K.;Egyeki,M.;Csik,G.Binding of Cationic Porphyrin to Isolated DNA and Nucleoprotein Complex:Quantitative Analysis of Binding Forms under Various Experimental Conditions.[J]Biochemistry,2005,44,15000-15006.
[10]Stang,P.J.;Olenyuk,B.Self-Assembly,Symmetry,and Molecular Architecture:Coordination as the Motif in the Rational Design of Supramolecular Metallacyclic Polygons and Polyhedra.Acc.Chem.Res.[J]1997,30,502-518.
[11](a) Imamura,T.;Fukushima,K.Self-assembly of metallopyridylporphyrin oligomers.[J]Coord.Chem.Rev.2000,198,133-156.
(b) Wojaczynski,J.;Latos-Grazynski,L.Poly- and oligometalloporphyrins associated through coordination.[J]Coord.Chem.Rev.2000,204,113-171.
[12]Suslick,K.S.;Bhyrappa,P.;Chou,J.-H.;Kosal,M.E.;Nakagaki,S.;Smithenry,D.W.;Wilson,S.R.Microporous Porphyrin Solids.[J]Acc.Chem.Res.2005,38,283-291.
[13]Yu,J.Mathew,S.Flavel,B.S.Johnston,M.R.Shapter,J.G.Ruthenium Porphyrin Functionalized Single-Walled Carbon Nanotube ArrayssA Step Toward Light Harvesting Antenna and Multibit Information Storage.[J]J.Am.Chem.Soc.2008,130,8788-8796.
[14]Takahashi,R.;Kobuke,Y.Hexameric Macroring of Gable-Porphyrins as a Light-Harvesting Antenna Mimic.[J]J.Am.Chem.Soc.2003,125,2372-2373.
[15]Kosal,M.E.;Chou,J.-H.;Wilson,S.R.;Suslick,K.S.[J]Nat.Mater.2002,1,118-121.
[16]Van Nostrum,C.F.;Nolte,R.J.M.Functional supramolecular materials:self-assembly of phthalocyanines and porphyrazines.[J]Chem.Commun.1996, 2385-2392.
[17]Engelkamp,H.;Middelbeek,S.;Nolte,R.J.M.Self-Assembly of Disk-Shaped Molecules to Coiled-Coil Aggregates with Tunable Helicity.[J]Science 1999,284,785-788.
[18]Elemans,J.A.A.W.;Rowan,A.E.;Nolte,R.J.M.Mastering molecular matter.Supramolecular architectures by hierarchical self-assembly.[J]J.Mater.Chem.2003,13,2661-2670.
[19]Samori,P.;Engelkamp,H.;de Witte,P.;Rowan,A.E.;Nolte,R.J.M.Rabe,J.P.Self-Assembly and Manipulation of Crown Ether Phthalocyanines at the Gel-Graphite Interface.[J]Angew.Chem.Int.Ed.2001,40,2348-2350.
[20]Samori,P.;Engelkamp,H.;de Witte,P.A.J.;Rowan,A.E.;Nolte,R.J.M.;Rabe,J.P.Self-Organization of Semiconducting Polysiloxane-Phthalocyanine on a Graphite Surface.[J]Adv.Mater.2005,17,1265-1268.
[21]Sly,J.;Kasak,P.Gomar-Nadal,E.;Rovira,C.;Gorriz,L.;Thordarson,P.;Amabilino,D.B.;Rowan,A.E.;Nolte,R.J.M.Chiral molecular tapes from novel tetra(thiafulvalene-crown-ether)-substituted phthalocyanine building blocks.[J]Chem.Commun.2005,1255-1257.
[22]Lu,G.;Chen,Y.;Zhang,Y.;Bao,M.;Bian,Y.;Li,X.;Jiang,J.Morphology Controlled Self-assembled Nanostructures of Sandwich Mixed (Phthalocyaninato)(porphyrinato) Europium Triple-deckers.Effect of Hydrogen Bonding on Tuning the Inter-molecular Interaction.[J]J.Am.Chem.Soc.2008,130,11623-11630.
[23]Gao,Y.;Zhang,X.;Ma.C.;Li,X.;Jiang,J.Morphology Controlled Self-assembled Nanostructures of 5,15-Di[4-(5-acetylsulfanylpentyloxy)phenyl]porphyrin Derivatives.Effect of Metal-Ligand Coordination Bonding on Tuning the Inter-molecular Interaction.[J]J.Am.Chem.Soc.2008,130,17044-17052.
[24]Konan,Y.N.;Cerny,R.;Favet,J.;Berton.M.;Gurny,R.;Allemann,E.Preparation and characterization of sterile sub-200 nm meso-tetra(4-hydroxylphenyl)porphyrin-loaded nanoparticles for photodynamic therapy.[J]Eur.J.Pharm.Biopharm.2003,55,115-124.
[25]Konan,Y.N.;Berton.M.;Gurny,R.;Allemann,E.Enhanced photodynamic activity of meso-tetra(4-hydroxyphenyl)porphyrin by incorporation into sub-200nm nanoparticles.[J]Eur.J.Pharm.Science.2003,18,241-249.
[26](a) Adler,A.D.;Longo,F.R.;Shergalis.W.Mechanistic Investigations of Porphyrin Syntheses.I.Preliminary Studies on ms-Tetraphenylporphinl.[J]J.Am.Chem.Soc.,1964,86,3145-3149.
(b) Adler,A.D.;Longo,F.R.;Finarelli,J.D.;Goldmacher,J.;Assour,J.;Korsakoff,L.A Simplified Synthesisfor msso-Tetraphenylporphin.[J]J.Org.Chem.1967,32,476-476.
[27](a) Guo,H.;Jiang,J.;Shi,Y.;Wang,Y.;Liu,J.;Dong,S.UV-Vis Spectrophotometric Titrations and Vibrational Spectroscopic Characterization of meso-(p-Hydroxyphenyl)porphyrins.[J]J.Phys.Chem.B.2004,108,10185-10191.
(b) Guo,H.;Jiang,J.;Shi,Y.;Wang,Y.;Wang,Y.;Dong,S.Sequential Deprotonation of meso-(p-Hydroxyphenyl)porphyrins in DMF:From Hyperporphyrins to Sodium Porphyrin Complexes.[J]J Phys.Chem.B.2006,110,587-594.
[28]Adler,A.D.;Longo,F.R.[J]J.Inorg.Nucl.Chem.1970,32,2443-2445.
[29](a) Gong,X.;Milic,T.;Xu,C.;Batteas,J.D.;Drain,C.M.Preparation and Characterization of Porphyrin Nanoparticles.[J]J.Am.Chem.Soc.2002,124,14290-14291.
(b) Maiti,N.C.;Mazumdar,S.;Periasamy,N,J- and H-Aggregates of Porphyrin-Surfactant Complexes:Time-Resolved Fluorescence and Other Spectroscopic Studies.[J]J.Phys.Chem.B 1998,102,1528-1538.
(c) Hunter,C.A.;Sanders,J.K.M.The Nature of π-π Interactions.[J]J.Am.Chem.Soc.1990,112,5525-5534.
(d) Kano,K.;Minamizono,H.;Kitae,T.;Negi,S.Self-Aggregation of Cationic Porphyrins in Water.Can(?)-(?) Stacking Interaction Overcome Electrostatic Repulsive Force.[J]J.Phys.Chem.A 1997,101,6118-6124.
(e) Purrello,R.;Monsu' Scolaro,L.;Bellacchio,E.;Gurrieri,S.;Romeo,A.Chiral H- and J-Type Aggregates of meso-Tetrakis(4-sulfonatophenyl)porphine on a-Helical Polyglutamic Acid Induced by Cationic Porphyrins.[J]Inorg.Chem.1998,37,3647-3648.
[30]Ulman,A.;Manassen,J.Synthesis of new tetraphenylporphyrin molecules containing heteroatoms other than nitrogen.I.Tetraphenyl-21,23-dithiaporphyrin.[J]J.Am.Chem.Soc.1975,97,6540-6544.
[31]Kasha,M.;Rawls,H.R.;EI-Bayoumi,M.A.[J]Pure Appl.Chem.1965,11, 371-392.
[32]Kano,K.;Fukuda,K.;Wakami,H.;Nishiyabu,R.;Pasternack,R.F.Factors Influencing Self-Aggregation Tendencies of Cationic Porphyrins in Aqueous Solution[J]J.Am.Chem.Soc.2000,122,7494-7502.
[33](a) Kimura,M.;Muto,T.;Takimoto,H.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai.H.;Kobayash,N.Fibrous Assemblies Made of Amphiphilic Metallophthalocyanines[J]Langmuir 2000,16,2078-2082.
(b) Kimura,M.;Kuroda,T.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Self-Organization of Hydrogen-Bonded Optically Active Phthalocyanine Dimers.[J]Langmuir 2003,19,4825-4830.
[34]Pan,J.;Nguyen,K.L.[J]Anal.Chem.2007,79,2259-2265.Sayed,M.B.[J]Ind.Eng.Chem.Res.2004,43,4822-4826.
[35]Balaban,T.S.;Linke-Schaetzel,M.;Bhise,A.D.;Vanthuyne,N.;Roussel,C.;Anson,C,E.;Buth,G.;Eichhofer,A.;Foster,K.;Garab,G.;Gliemann,H.;Goddard,R.;Javorfi,T.;Powell,A.K.;Rosner,H.;Schimmel,T.Structural Characterization of Artificial Self-Assembling Porphyrins That Mimic the Natural Chlorosomal Bacteriochlorophylls c,d,and e.[J]Chem.Eur.J.2005,11,2267-2275.
[36](a) Caruso,F.;Caruso,A.R.;M(o|¨)hwald,H.Nanoengineering of Inorganic and Hybrid Hollow Spheres by Colloidal Templating.[J]Science 1998,282,1111-1114.
(b) Caruso,F.Nanoengineering of Particle Surfaces.[J]Adv.Mater.2001,13,11-22.
(c) Ma,Y.R.;Qi,L.M.;Ma,J.M.;Cheng,H.M.Facile Synthesis of Hollow ZnS Nanospheres in Block Copolymer Solutions.[J]Langmuir 2003,19,4040-4042.
(d) Nakashima,T.;Kimizuka,N.Interracial Synthesis of Hollow TiO_2Microspheres in Ionic Liquids.[J]J.Am.Chem.Soc.2003,125,6386-6387.
[37]Kano,K.;Fukuda,K.;Wakami,H.;Nishiyabu,R.;Pasternack,R.F.Factors Influencing Self-Aggregation Tendencies of Cationic Porphyrins in Aqueous Solution.[J]J.Am.Chem.Soc.2000,122,7494-7502.
[38]Minch,B.A.;Xia,W.;Donley,C.L.;Hernandez,R.M.;Carter,C.;Carducci,M.D.;Dawson,A.;O'Brien,D.F.;Armstrong,N.R.Octakis(2-benzyloxyethylsulfanyl) Copper(Ⅱ) Phthalocyanine:A New Liquid Crystalline Discotic Material with Benzyl-Terminated,Thioether-Linked Side Chains.[J]Chem.Mater.2005,17,1618-1627.
[39]Belarbi,Z.;Sirlin,C.;Simon,J.;Andre,J.J.[J]J.Phys.Chem.1989,93,8105-8110.
[40]Kimura,M.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Organic-Inorganic Composites Comprised of Ordered Stacks of Amphiphilic Molecular Disks.[J]J.Am.Chem.Soc.2001,123,2438-2439.
[41]Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Montgomery,J.A.,Jr.;Vreven,T.;Kudin,K.N.;Burant,J.C.;Millam,J.M.;Iyengar,S.S.;Tomasi,J.;Barone,V.;Mennucci,B.;Cossi,M.;Scalmani,G.;Rega,N.;Petersson,G.A.;Nakatsuji,H.;Hada,M.;Ehara,M.;Toyota,K.;Fukuda,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Klene,M.;Li,X.;Knox,J.E.;Hratchian,H.P.;Cross,J.B.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Ayala,P.Y.;Morokuma,K.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Zakrzewski,V.G.;Dapprich,S.;Daniels,A.D.;Strain,M.C.;Farkas,O.;Malick,D.,K.;Rabuck,A.D.;Raghavachari,K.;Foresman,J.B.;Ortiz,J.V.;Cui,Q.;Baboul,A.G.;Clifford,S.;Cioslowski,J.;Stefanov,B.B.;Liu,G.;Liashenko,A.;Piskorz,P.;Komaromi,I.;Martin,R.L.;Fox,D.J.;Keith,T.;Al-Laham,M.A.;Peng,C.Y.;Nanayakkara,A.;Challacombe,M.;Gill,P.M.W.;Johnson,B.;Chen,W.;Wong,M.W.;Gonzalez,C.;Pople,J.A.Gaussian 03,Revision B.05;Gaussian,Inc.:Pittsburgh,PA,2003.
[42](a) Diskin-Posner,Y.;Patra,G.K.;Goldberg,I.Supramolecular porphyrin-based materials.Assembly modes of [5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrinato]zinc with bipyridyl ligands.[J]CrystEngComm.2002,4,296-301.
(b) Krishna Kumar,R.;Balasubramanian,S.;Goldberg,I.Supramolecular Multiporphyrin Architecture.Coordination Polymers and Open Networks in Crystals of Tetrakis(4-cyanophenyl)- and Tetrakis(4-nitrophenyl)metalloporphyrin.[J]Inorg.Chem.1998,37,541-552.
(c)Mazzanti,M.;Veyrat,M.;Ramasseul,R.;Marchon,J.-C.;Turowska-Tyrk,I.;Shang,M.;Scheidt,W.R.A New Ruthenium(Ⅱ) Chiroporphyrin Containing a Multipoint Recognition Site:Enantioselective Receptor of Chiral Aliphatic Alcohols.[J]Inorg.Chem.1996,35,3733-3734.
(d) Barkigia,K.M.;Rennet,M.W.;Senge,M.O.;Fajer,J.Interplay of Axial Ligation,Hydrogen Bonding, Self-Assembly,and Conformational Landscapes in High-Spin Ni(Ⅱ) Porphyrins[J]J.Phys.Chem.B.2004,108,2173-2180.
[43]Antonietti,M.;F(O|¨)rster,S.Vesicles and Liposomes:A Self-Assembly Principle Beyond Lipids.[J]Adv.Mater.2003,15,1323-1333.
[44]Yang,Y.-F.;Ma,Y.-S.;Guo,L.-R.;Zheng,L.-M.Copper Phosphonates based on 2-Phosphonic-isonicotinate:Structures and Magnetic Properties.[J]Cryst.Growth Des.2008,8,1213-1217.
[45]Goldberg,I.;Krupitsky,H.;Stein,Z.;Hsiou,Y.;Strouse,C.E.[J]Supramolecular Chemistry 1994,4,203-209.
[46]Balaban.T.S.;Eichh(o|¨)fer,A.;Lehn,J.-M.Self-Assembly by Hydrogen Bonding and π-π Interactions in the Crystal of a Porphyrin π-π Attempts to Mimic Bacteriochlorophyll c.[J]Eur.J.Org.Chem.2000,4047-4057.
[47]Bonifazia,D.;Accorsic,G.;Armaroli,N.;Songb,F.;Palkarb,A.;Echegoyen.L.;Scholla,M.;Seilera,P.;Jauna,B.;Diederich,F.[J]Helvetica Chimica.Acta.2005,88,1839-1884.
[48]Bolis,V.;Maggiorini,S.;Meda,L.;D'Acapito,F.;Turnes Palomino,G.;Bordiga,S.;Lamberti,C.[J]J.Chem.Phys.2000,113,9248-9261.
[1]Elemans,J.A.A.W.;Hameren,R.van;Nolte,R.J.M.;Rowan,A.E.Molecular Materials by Self-Assembly of Porphyrins,Phthalocyanines,and Perylenes.[J]Adv.Mater.2006,18,1251-1226.
[2](a) Hartgerink,J.D.;Beniash,E.;Stupp,S.Self-Assembly and Mineralization of Peptide-Amphiphile Nanopbers I.[J]Science 2001,294,1684-1688.
(b) Kitamura,T.;Nakaso,S.;Mizoshita,N.;Tochigi,Y.;Shimomura,T.;Moriyama,M.;Ito,K.;Kato,T.Electroactive Supramolecular Self-Assembled Fibers Comprised of Doped Tetrathiafulvalene-Based Gelators.[J]J.Am.Chem.Soc.2005,127,14769-14775.
[3]Schwab,A.D.;Smith,D.E.;Bond-Watts,B.;Johnston,D.E.;Hone,J.;Johnson,A.T.;de Paula,J.C.;Smith,W.F.Photoconductivity of Self-Assembled Porphyrin Nanorods.[J]Nano.Lett.2004,4,1261-1265.
[4]Wang,Z.;Li,Z.;Medforth,C.J.;Shelnutt,J.A.Self-Assembly and Self-Metallization of Porphyrin Nanosheets.[J]J.Am.Chem.Soc.2007,129,2440-2441.
[5](a) Yan,D.Y.;Zhou,Y.F.;Hou,J.Supramolecular Self-Assembly of Macroscopic Tubes.[J]Science 2004,303,65-67.
(b) Shimizu,T.;Masuda,M.;Minamikawa,H.Supramolecular Nanotube Architectures Based on Amphiphilic Molecules.[J]Chem.Rev.2005,105,1401-1444.
(c) Zhi,L.;Gorelik,T.;Wu,J.;Kolb,U.;M(u|¨)llen,K.Nanotubes Fabricated from Ni-Naphthalocyanine by a Template Method.[J]J.Am.Chem.Soc.2005,127,12792-12793.
(d) Hu,J.-S.;Guo,Y.-G.;Liang,H.-P.;Wan,L.-J.;Jiang,L.Three-Dimensional Self-Organization of Supramolecular Self-Assembled Porphyrin Hollow Hexagonal Nanoprisms[J]J.Am.Chem.Soc.2005,127,17090-17095.
[6]Liu,R.;Holman,M.W.;Zang,L.;Adams,D.M.Single-Molecule Spectroscopy of Intramolecular Electron Transfer in Donor-Bridge-Acceptor Systems.[J]J.Phys.Chem.A.2003,107,6522-6526.
[7]Holman,M.W.;Liu,R.;Zang,L.;Yan,P.;DiBenedetto,S.A.;Bowers,R.D.;Adams,D.M.Studying and Switching Electron Transfer:From the Ensemble to the Single Molecule.[J]J.Am.Chem.Soc.2004,126,16126-16133.
[8]Sauer,M.Single-Molecule-Sensitive Fluorescent Sensors Based on Photoinduced Intramolecular Charge Transfer.[J]Angew.Chem.,Int.Ed.2003,42,1790-1793.
[9]Grimsdale,A.C.;M(u|¨)llen,K.The Chemistry of Organic Nanomaterials.[J]Angew.Chem.Int.Ed.2005,44,5592-5629.
[10]Xu,B.Q.;Xiao,X.;Yang,X.;Zang,L.;Tao,N.J.Large Gate Modulation in the Current of a Room Temperature Single Molecule Transistor.[J]J.Am.Chem.Soc.2005,127,2386-2387.
[11]Li,X.;Xu,B.Q.;Xiao,X.;Yang,X.;Zang,L.;Tao,N.J.Controlling charge transport in single molecules using electrochemical gate.[J]Faraday Discuss.2006,131,111-120.
[12](a) Chen,Y.;Su,W.;Bai,M.;Jiang,J.;Li,X.;Liu,Y.;Wang,L.;Wang,S.High Performance Organic Field-Effect Transistors Based on Amphiphilic Tris(phthalocyaninato) Rare Earth Triple-Decker Complexes.[J]J.Am.Chem.Soc.2005,127,15700-15701.
(b) Li,R.;Ma,P.;Dong,S.;Zhang,X.;Chen,Y.;Li,X.;Jiang,J.Synthesis,Characterization,and OFET Properties of Amphiphilic Heteroleptic Tris(phthalocyaninato) Europium(Ⅲ) Complexes with Hydrophilic Poly(oxyethylene)Substituents.[J]Inorg.Chem.2007,46,11397-11404.
[13]Schmidt-Mende,L.;Fechtenk(o|¨)tter,A.;M(u|¨)llen,K.;Moons,E.;Friend,R.H.;MacKenzie,J.D.Self-Organized Discotic Liquid Crystals for High-Efficiency Organic Photovoltaics.[J]Science 2001,293,1119-1122.
[14]Gregg,B.A.Excitonic Solar Cells.[J]J.Phys.Chem.B.2003,107,4688-4698.
[15]Gregg,B.A.Evolution of Photophysical and Photovoltaic Properties of Perylene Bis(phenethylimide) Films upon Solvent Vapor Annealing.[J]J.Phys.Chem.1996,100,852-859.
[16]Tamizhmani,G.;Dodelet,J.P.;Cote,R.;Gravel,D.Photoelectrochemical Characterization of Thin Films of Perylenetetracarboxylic Acid Derivatives[J]Chem.Mater.1991,3,1046-1053.
[17]Liu,Y.;Xiao,S.;Li,H.;Li,Y.;Liu,H.;Lu,F.;Zhuang,J.;Zhu,D.Self-Assembly and Characterization of A Novel Hydrogen-Bonded Nanostructure.[J]J.Phys.Chem.B.2004,108,6256-6260.
[18]Peeters,E.;Van Hal,P.A.;Meskers,S.C.J.;Janssen,R.A.J.;Meijer,E.W.Photoinduced Electron Transfer in a Mesogenic Donor-Acceptor-Donor System.[J]Chem.Eur.J.2002,8,4470-4474.
[19]Yokoyama,T.;Yokoyama,S.;Kamikado,T.;Yoshishige Okuno,Y.;Mashiko,T.Selective assembly on a surface of supramolecular aggregates with controlled size and shape.[J]Nature 2001,413,619-621.
[20]Balakrishnan,K.;Datar,A.;Naddo,T.;Huang,J.;Oitker,R.;Yen,M.;Zhao,J.;Zang,L.Nanobelt Self-Assembly from an Organic n-Type Semiconductor:Propoxyethyl-PTCDI.[J]J.Am.Chem.Soc.2006,128,7390-7398.
[21]Su,W.;Zhang,Y.;Zhao,C.;Li,X.;Jiang,J.Self-Assembled Organic Nanostructures:Effectof Substituents on the Morphology.[J]ChemPhysChem.2007,8,1857-1862.
[22](a) Hamza I.Intracellular Trafficking of Porphyrins.[J]ACS Chem.Biol.2006,1,627-629.
(b) Lo,P.-C.;Chan,C.M.H.;Liu,J.-Y.;Fong,W.-P.;Ng,D.K.P.Highly Photocytotoxic Glucosylated Silicon(Ⅳ) Phthalocyanines.Effects of Peripheral Chloro Substitution on the Photophysical and Photodynamic Properties[J]J.Med.Chem.2007,50,2100-2107.
(c) Vanyur,R.;Heberger,K.;Jakus,J.Prediction of Anti-HIV-1 Activity of a Series of Tetrapyrrole Molecules.[J]J.Chem.Inf.Comput.Sci.2003,43,1829-1836.
[23]Li,Y.;Li,X.;Li,Y:Liu,H.;Wang,S.;Gan,H.;Li,J.;Wang,N.;He,X.;Zhu,D.Controlled Self-Assembly Behavior of an Amphiphilic Bisporphyrin-Bipyridinium-Palladium Complex:From Multibilayer Vesiclesto Hollow Capsules.[J]Angew.Chem.Int.Ed.2006,45,3639-3643.
[24]Wang,Z.;Medforth,C.J.;Shelnutt,J.A.Porphyrin Nanotubes by Ionic Self-Assembly.[J]J.Am.Chem.Soc.2004,126,15954-15955.
[25]Shirakawa,M.;Kawano,S.-i.;Fujita,N.;Sada,K.;Shinkai S.Hydrogen-Bond-Assisted Control of H versus J Aggregation Mode of Porphyrins Stacks in an Organogel System.[J]J.Org.Chem.2003,68,5037-5044.
[26]Kimura,M.;Muto,T.;Takimoto,H.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai.H.;Kobayash,N.Fibrous Assemblies Made of Amphiphilic Metallophthalocyanines.[J]Langmuir 2000,16,2078-2082.
[27]Engelkamp,H.;Middelbeek,S.;Nolte,R.J.M.Science Magazine Search Results.[J]Science 1999,284,785-788.
[28]See for example(a) Jiang,J.;Ng,D.K.P.A Decade Journey in the Chemistry of Sandwich-Type Tetrapyrrolato Rare Earth Complexes.[J]Acc.Chem.Res.2009,42,79-88.
(b) Jiang,J.;Bao,M.;Rintoul,L.;Arnold,D.P.Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes.[J]Coord.Chem.Rev.2006,250,424-448.
(c) Jiang, J.;Kasuga,K.;Arnold,D.P.In Supramolecular Photosensitive and Electroactive Materials;[M]Nalwa,H.S.,Ed.;Academic Press:New York,2001;Chapter 2,pp 113-210.
(d) Ng,D.K.P.;Jiang,J.Sandwich-Type Heteroleptic Phthalocyaninato and Porphyrinato Metal Complexes.[J]Chem.Soc.Rev.1997,26,433-442.
(e) Yoshimoto,S.;Sawaguchi,T.;Su,W.;Jiang,J.;Kobayashi,N.Superstructure Formation and Rearrangement in the Adlayer of a Rare-Earth-Metal Triple-Decker Sandwich Complex at the Electrochemical Interface.[J]Angew.Chem.Int.Ed 2007,46,1071-1074.
(f) Ye,T.;Takami,T.;Wang,R.;Jiang,J.;Weiss,P.S.Tuning Interactions between Ligands in Self-Assembled Double-Decker Phthalocyanine Arrays[J]J.Am.Chem.Soc.2006,128,10984-10985.
[29]Liu,Q.;Li,Y.;Liu,H.;Chen,Y.;Wang,X.;Zhang,Y.;Li,X.;Jiang,J.Nanotubes Fabricated from Sandwich-Type Mixed(Porphryinato)(phthalocyaninato)europium Complex by Template Technique.[J]J.Phys.Chem.C.2007,111,7298-7301.
[30](a) Kirin,I.S.;Moskalev,P.N.;Makashev,Y.A.[J]Russ.J.Inorg.Chem.1965,10,1065-1066.
(b) Buchler,J.W.;Ng,D.K.P.In The Porphyrin Handbook;Kadish,K.M.,Smith,K.M.,Guilard,R.,Eds.;[M]Academic Press:San Diego,2000,Vol.3,pp 245-294.
(c) Sun,X.;Cui,X.;Arnold,D.P.;Choi,M.T.M.;Ng,D.K.P.;Jiang,J.The Electronic Absorption Characteristics of Mixed Phthalocyaninato Porphyrinato Rare Earth(Ⅲ) Triple-Deckers M2(TPyP)2(Pc).[J]Eur.J.Inorg.Chem.2003,8,1555-1561.
(d) Sun,X.;Li,R.;Wang,D.;Dou,J.;Zhu,P.;Lu,F.;Ma,C.;Choi,Ch-F.;Cheng,D.Y.Y.;Ng,D.K.P.;Kobayashi,N.;Jiang,J.Synthesis and Characterization of Mixed Phthalocyaninato and meso-Tetrakis(4-chlorophenyl)porphyrinato Triple-Decker Complexes-Revealing the Origin of Their Electronic Absorptions.[J]Eur.J.Inorg.Chem.2004,19,3806-3813.
[31]Kasha,M.;Rawls,H.R.;EI-Bayoumi,M.A.[J]Pure Appl.Chem.1965,11,371-392.
[32]Kimura,M.;Kuroda,T.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Self-Organization of Hydrogen-Bonded Optically Active Phthalocyanine Dimers.[J]Langmuir 2003,19,4825-4830.
[33]Minch,B.A.;Xia,W.;Donley,C.L.;Hernandez,R.M.;Carter,C.;Carducci,M.D.;Dawson,A.;O'Brien,D.F.;Armstrong,N.R.Octakis(2-benzyloxyethylsulfanyl) Copper (Ⅱ) Phthalocyanine:A New Liquid Crystalline Discotic Material with Benzyl-Terminated,Thioether-Linked Side Chains.[J]Chem.Mater.2005,17,1618-1627.
[34]Belarbi,Z.;Sidin,C.;Simon,J.;Andre,J.J.[J]J.Phys.Chem.1989,93,8105-8110.
[35]Kimura,M.;Wada,K.;Ohta,K.;Hanabusa,K.;Shirai,H.;Kobayashi,N.Organic-Inorganic Composites Comprised of Ordered Stacks of Amphiphilic Molecular Disks.[J]J.Am.Chem.Soc.2001,123,2438-2439.
[36]Kobayashi,T;Isoda,S.Lattice images and molecular images of organic materials.[J]J.Mater.Chem.1993,3,1-14.
[37](a) Petritsch,K.;Friend,R.H.;Lux,A.;Rozenberg,G.G.;Moratti,S.C.;Holmes,A.B.Liquid crystalline phthalocyanines in organic solar cells.[J]Synth.Met.1999,102,1776-1777.
(b) Handbook of Liquid Crystals;Demus,D.;Goodby,J.;Gray,G.W.;Spiess,H.-W.,Eds.;[M]Wiley-VCH:New York,1998;Vol.1:Fundamentals.
[38]Hoeben,F.J.M.;Jonkheijm,P.;Meijer,E.W.;Schenning,A.P.H.J.About Supramolecular Assemblies of x-Conjugated Systems.[J]Chem.Rev.2005,105,1491-1546.
[39]Babel,A.;Jenekhe,S.A.High Electron Mobility in Ladder Polymer Field-Effect Transistors.[J]J.Am.Chem.Soc.2005,125,13656-13657.
[40]Bian,Y.;Jiang,J.;Tao,Y.;Choi,M.T.M.;Li,R.;Ng,A.C.H.;Zhu,P.;Pan,N.;Sun,X.;Arnold,D.P.;Zhou,Z.;Li,H.-W.;Mak,T.C.W.;Ng,D.P.K.[J]J.Am.Chem.Soc.2003,125,12257-12267.
[41]Little,R.G.[J]J.Heter.Chem.1978,15,203-208.
[42]Littler,B.J.;Ciringh,Y.;Lindsey,J.S.Investigation of Conditions Giving Minimal Scrambling in the Synthesis of trans-Porphyrins from Dipyrromethanes and Aldehydes.[J]J.Org.Chem.1999,64,2864-2872.
[43]Stites,J.G.;McCarty,C.N.;Quill,L.L.The Rare Earth Metals and their Compounds.Ⅷ.An Improved Method for the Synthesis of Some Rare Earth Acetylacetonates.[J]J.Am.Chem.Soc.1948,70,3142-3143.
[44]Jiang,J.;Liu,R.C.W.;Mak,T.C.W.;Chan,T.W.D.;Ng,D.K.P.Synthesis,spectroscopic and electrochemical properties of substituted bis(phthalocyaninato)lanthanide(Ⅲ) complexes.[J]Polyhedron 1997,16,515-520.
[45]Gong,X.;Milic,T.;Xu,C.;Batteas,J.D.;Drain,C.M.Preparation and Characterization of Porphyrin Nanoparticles.[J]J.Am.Chem.Soc.2002,124,14290-12491.
[1][1a]J.Jiang,K.Kasuga,D.P.Arnold in Supramolecular Photo-sensitive and Electro-active Materials(Ed.:H.S.Nalwa),[M]Academic Press,New York,2001,pp.113-210.
[1b]D.K.P.Ng,J.Jiang,K.Kasuga,K.Machida in Handbook on the Physics and Chemistry of Rare Earths(Ed.:K.A.Gschneidner,Jr.,L.Eyring,G.H.Lander),[M]Elsevier,Amsterdam,2001,pp.611-654.
[1c]R.Weiss,J.Fischer in The Porphyrin Handbook,Vol.16(Eds.:K.M.Kadish,K.M.Smith,R.Guilard),[M]Academic Press,San Diego,2003,pp.172-246.
[1d]y.Chen,W.Su,M.Bai,J.Jiang,X.Li,Y.Liu,L.Wang,S.Wang,High Performance Organic Field-Effect Transistors Based on Amphiphilic Tris(phthalocyaninato) Rare Earth Triple-Decker Complexes.[J]J.Am.Chem.Soc.2005,127,15700-15701.
[2]J.Jiang,W.Liu,D.P.Arnold,Sandwich complexes of naphthalocyanine with the rare earth metals.[J]J.Porphyrins Phthalocyanines 2003,7,459-473.
[3]D.K.P.Ng,J.Jiang,Sandwich-type heteroleptic phthalocyaninato and porphyrinato metal complexes.[J]Chem.Soc.Rev.1997,26,433-442.
[4][4a]K.H.Yew,H.J.Koh,H.W.Lee,I.Lee,[J]J.Chem.Soc.,Perkin Trans.2 1995,2263-2268.
[4b]T.Itoh,R.Noki,S.Simosato,I.Magara,S.Iwatsuki,[J]J.Polymer Science,Part A:Polymer Chemistry 1995,33,1475-1485.
[5]U.Diefenbach,H.R.Allcock,Synthesis of Cyclo- and Polyphosphazenes with Pyridine Side Groups.[J]Inorg.Chem.1994,33,4562-4565.
[6]R.Li,X.Zhang,P.Zhu,D.K.P.Ng,N.Kobayashi,J.Jiang,Electron-Donating or -Withdrawing Nature of Substituents Revealed by the Electrochemistry of Metal-Free Phthalocyanines.[J]Inorg.Chem.2006,45,2327-2334.
[7]A.Pondaven,Y.Cozien,M.L'Her,[J]New.J.Chem.1991,15,515-516.
[8]A.Pondaven,Y.Cozien,M.L'Her,[J]New.J.Chem.1992,16,711-718.
[9][9a]F.Guyon,A.Pondaven,P.Guenot,M.L'Her,Bis(2,3-naphthalocyaninato)lutetium(Ⅲ) and (2,3-Naphthalocyaninato)(phthalocyaninato)lutetium(Ⅲ) Complexes:Synthesis,Spectroscopic Characterization,and Electrochemistry.[J]Inorg.Chem.1994,33,4787-4793.
[9b]C.Cadiou,A.Pondaven,M.L'Her,P.Jehan,P.Guenoy,An Amphiphilic Lutetium Bisphthalocyanine:Lu[(PEO)4Pc][(DodO)4Pc][J]J.Org.Chem.1999,64, 9046-9050.
[9c]L.Gaimiche,F.Guyon,A.Pondaven,J.-Y.Moisan,M.L'Her.Photogeneration of charges in poly(N-vinylcarbazole) doped with lutetium bisphthalocyanines and lutetium bisnaphthalocyanines.[J]J.Porphyrins and Phthalocyanines 2003,7,382-387.
[10][10a]J.Jiang,W.Liu,W.Law,J.Lin,D.P.Arnold,A new synthetic route to unsymmetrical bis(phthalocyaninato)europium(Ⅲ) complexes.[J]Inorg.Chem.Acta 1998,268,141-144.
[10b]J.Jiang,J.Xie,M.T.M.Choi,D.K.P.Ng,Double-decker yttrium(Ⅲ) complexes with phthalocyaninato and porphyrinato ligands.[J]J.Porphyrins Phthalocyanines 1999,3,322-328.
[10c]Y.Bian,R.Wang,J.Jiang,C.-H.Lee,J.Wang and D.K.P.Ng,Synthesis,spectroscopic characterisation and structure of the first chiral heteroleptic bis(phthalocyaninato) rare earth complexes.[J]Chem.Commun.2003,1194-1195.
[10d]J.Jiang,R.C.W.Liu,T.C.W.Mak,T.W.D.Chan,D.K.P.Ng,Synthesis,spectroscopic and electrochemical properties of substituted bis(phthalocyaninato)lanthanide(Ⅲ) complexes.[J]Polyhedron 1997,16,515-520.
[11][11a]J.Jiang,D.P.Arnold,H.Yu,Infra-red spectra of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes[J]Polyhedron 1999,18,2129-2139.
[11b]X.Sun,M Bao,N.Pan,X Cui,D.P.Arnold,J.Jiang,[J]Aust.J.Chem.2002,9,587-595.
[11c]F.Lu,M.Bao,C.Ma,X.Zhang,D.P.Arnold,J.Jiang,[J]Spectrochim Acta Part A 2003,59,3273-3286.
[11d]M.Bao,N.Pan,C.Ma,D.P.Arnold,J.Jiang,Infrared spectra of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes:Part 4.The infrared characteristics of phthalocyanine in heteroleptic tris(phthalocyaninato) rare earth complexes.[J]Vibrational Spectroscopy 2003,32,175-184.
[11e]M.Bao,Y.Bian,L.Rintoul,R.Wang,D.P.Arnold,C.Ma,J.Jiang,Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type (na)phthalocyaninato and porphyrinato rare earth complexes:(Part 10) The infrared and Raman characteristics of phthalocyanine in heteroleptic bis(phthalocyaninato) rare earth complexes with decreased molecular symmetry[J]Vibrational Spectroscopy 2004,34,283-291.
[11f]J.Jiang,M.L.Rintoul,D.P.Arnold,Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type(na)phthalocyaninato and porphyrinato rare earth complexes.[J]Coord.Chem.Rev.2006,250,424-448.
[12]Y.Bian,J.Jiang,Y.Tao,M.T.M.Choi,R.Li,A.C.H.Ng,P.Zhu,N.Pan,X.Sun,D.P. Arnold,Z.Zhou,H.-W.Li,D.K.P.Ng,Tuning the Valence of the Cerium Center in (Na)phthalocyaninato and Porphyrinato Cerium Double-Deckers by Changing the Nature of the Tetrapyrrole Ligands.[J]J.Am.Chem.Soc.2003,125,12257-12267.
[13]J.Jiang,Y Bian,F.Furuya,W.Liu,M.T.M.Choi,N.Kobayashi,H.-W.Li,Q.Yang,T.C.W.Male,D.K.P.Ng,Synthesis,Structure,Spectroscopic Properties,and Electrochemistry of Rare Earth Sandwich Compounds with Mixed 2,3-Naphthalocyaninato and Octaethylporphyrinato Ligands.[J]Chem.Eur.J.2001,7,5059-5069.
[14]J.Jiang,W.Liu,K.-L.Cheng,K.-W.Poon,D.K.P.Ng,Heteroleptic Rare Earth Double-Decker Complexes with Porphyrinato and 2,3-Naphthalocyaninato Ligands-Preparation,Spectroscopic Characterization,and Electrochemical Studies.[J]Eur.J.Inorg.Chem.2001,413-417.
[15]F.Lu,X.Sun,R.Li,D.Liang,P.Zhu,X.Zhang,C.-F.Choi,D.K.P.Ng,T.Fukuda,N.Kobayashi,J.Jiang,Synthesis,spectroscopic properties,and electrochemistry of heteroleptic rare earth double-decker complexes with phthalocyaninato and meso-tetrakis(4-chlorophenyl)porphyrinato ligands.[J]New J.Chem.2004,28,1116-1122.
[16]P.Zhu,F.Lu,N.Pan,D.P.Arnold,S.Zhang,J.Jiang,J.Comparative Electrochemical Study of Unsubstituted and Substituted Bis(phthalocyaninato) Rare Earth(Ⅲ)Complexes.[J]Eur.J.Inorg.Chem.2004,510-517.
[17]~([17a]) E.Orti,J.L.Bredas,[J]J.Chem.Phys 1990,92,1228-1235.
~([17b]) N.Ishikawa,Electronic structures and spectral properties of double-and triple-decker phthalocyanine complexes in a localized molecular orbital view.[J]J.Porphyrins Phthalocyanines 2001,5,87-101.
[18]J.G.Stites,C.N.McCarty,L.L.Quill,The Rare Earth Metals and their Compounds.Ⅷ.An Improved Method for the Synthesis of Some Rare Earth Acetylacetonates.[J]J.Am.Chem.Soc.1948,70,3142-3143.
[19]D.Wohrle,M.Eskes,K.Shigehara,A.Yamada,[J]Synthesis 1993,194-196.
[20]~([20a]) J.J.p.Stewart,[J]J.Comp.Chem.1989,10,209-220.
~([20b]) J.J.p.Stewart,[J]J.Comp.Chem.1989,10,221-264.
[21]X.Zhang,Y.Zhang,J.Jiang,[J]J.Mol.Struct.THEOCHEM,,2004,673,103-108.
[22]M.J.Frisch et al.,Gaussian-98,Revision A.9,Gaussian,Inc.,Pittsburgh PA,1998.
[23] SMART and SAINT for Windows NT Software Reference Manuals, [M] Version 5.0, Bruker Analytical X-Ray Systems, Madison, WI, 1997.
[24] G. M. Sheldrick, SADABS - A Software for Empirical Absorption Correction, [M] University of Gottingen, 1997.
[25] SHELXL Reference Manual, [M] Version 5.1, Bruker Analytical X-Ray Systems, Madison, WI, 1997.
[1]~([1a]) J.Jiang,K.Kasuga,D.P.Arnold in Supramolecular Photo-sensitive and Electro-active Materials(Ed.:H.S.Nalwa),Academic Press,New York,2001,pp.113-210.
~([1b]) D.K.P.Ng,J.Jiang,K.Kasuga,K.Machida in Handbook on the Physics and Chemistry of Rare Earths(Ed.:K.A.Gschneidner,Jr.,L.Eyring,G.H.Lander),Elsevier,Amsterdam,2001,pp.611-654.
~([1c]) R.Weiss,J.Fischer in The Porphyrin Handbook,Vol.16(Eds.:K.M.Kadish,K.M.Smith,R.Guilard),Academic Press,San Diego,2003,pp.172-246.
~([1d]) y.Chen,W.Su,M.Bai,J.Jiang,X.Li,Y.Liu,L.Wang,S.Wang,J.Am.Chem.Soc.2005,127,15700-15701.
[2]J.Jiang,W.Liu,D.P.Arnold,J.Porphyrins Phthalocyanines 2003,7,459-473.
[3]D.K.P.Ng,J.Jiang,Chem.Soc.Rev.1997,26,433-442.
[4]~([4a]) K.H.Yew,H.J.Koh,H.W.Lee,I.Lee,J.Chem.Soc.,Perkin Trans.2 1995,2263-2268.
~([4b]) T.Itoh,R.Noki,S.Simosato,I.Magara,S.Iwatsuki,J.Polymer Science,Part A:Polymer Chemistry 1995,33,1475-1485.
[5]U.Diefenbach,H.R.Allcock,Inorg.Chem.1994,33,4562-4565.
[6]R.Li,X.Zhang,P.Zhu,D.K.P.Ng,N.Kobayashi,J.Jiang,Inorg.Chem.2006,45,2327-2334.
[7]A.Pondaven,Y.Cozien,M.L'Her,New.J.Chem.1991,15,515-516.
[8]A.Pondaven,Y.Cozien,M.L'Her,New.J.Chem.1992,16,711-718.
[9]
~([9a]) F.Guyon,A.Pondaven,P.Guenot,M.L'Her,Inorg.Chem.1994,33,4787-4793.
~([9b])C.Cadiou,A.Pondaven,M.L'Her,P.Jehan,P.Guenoy,J.Org.Chem.1999,64,9046-9050.
~([9c]) L.Gaimiche,F.Guyon,A.Pondaven,J.-Y.Moisan,M.L'Her.J.Porphyrins and Phthalocyanines 2003,7,382-387.
[10]~([10a]) J.Jiang,W.Liu,W.Law,J.Lin,D.P.Arnold,Inorg.Chem.Acta 1998,268,141-144.
~([10b]) J.Jiang,J.Xie,M.T.M.Choi,D.K.P.Ng,J.Porphyrins Phthalocyanines 1999,3,322-328.
~([10c]) y.Bian,R.Wang,J.Jiang,C.-H.Lee,J.Wang and D.K.P.Ng,Chem.Commun.2003,1194-1195.
~([10d]) J.Jiang,R.C.W.Liu,T.C.W.Mak,T.W.D.Chan,D.K.P.Ng,Polyhedron 1997,16,515-520.
[11]~([11a]) J.Jiang,D.P.Arnold,H.Yu,Polyhedron 1999,18,2129-2139.
~([11b]) X.Sun,M Bao,N.Pan,X Cui,D.P.Arnold,J.Jiang,Aust.J.Chem.2002,9,587-595.
~([11c]) F.Lu,M.Bao,C.Ma,X.Zhang,D.P.Arnold,J.Jiang,Spectrochim Acta Part A 2003,59,3273-3286.
~([11d]) M.Bao,N.Pan,C.Ma,D.P.Arnold,J.Bang,Vibrational Spectroscopy 2003,32,175-184.
~[11e]) M.Bao,Y.Bian,L.Rintoul,R.Wang,D.P.Arnold,C.Ma,J.Jiang,Vibrational Spectroscopy 2004,34,283-291.
~([11f]) J.Jiang,M.L.Rintoul,D.P.Arnold,Coord.Chem.Rev.2006,250,424-448.
[12]Y.Bian,J.Jiang,Y.Tao,M.T.M.Choi,R.Li,A.C.H.Ng,P.Zhu,N.Pan,X.Sun,D.P.Arnold,Z.Zhou,H.-W.Li,D.K.P.Ng,J.Am.Chem.Soc.2003,125,12257-12267.
[13]J.Jiang,Y.Bian,F.Furuya,W.Liu,M.T.M.Choi,N.Kobayashi,H.-W.Li,Q.Yang,T.C.W.Mak,D.K.P.Ng,Chem.Eur.J.2001,7,5059-5069.
[14]J.Jiang,W.Liu,K.-L.Cheng,K.-W.Poon,D.K.P.Ng,Eur.J.Inorg.Chem.2001,413-417.
[15]F.Lu,X.Sun,R.Li,D.Liang,P.Zhu,X.Zhang,C.-F.Choi,D.K.P.Ng,T.Fukuda,N. Kobayashi,J.Jiang,New J.Chem.2004,28,1116-1122.
[16]P.Zhu,F.Lu,N.Pan,D.P.Arnold,S.Zhang,J.Jiang,J.Eur.J.Inorg.Chem.2004,510-517.
[17]~([17a]) E.Orti,J.L.Bredas,J.Chem.Phys.1990,92,1228-1235.
[17b]N.Ishikawa,J.Porphyrins Phthalocyanines 2001,5,87-101.
[18]J.G.Stites,C.N.McCarty,L.L.Quill,J.Am.Chem.Soc.1948,70,3142-3143.
[19]D.Wohrle,M.Eskes,K.Shigehara,A.Yamada,Synthesis 1993,194-196.
[20]~([20a]) J.J.P.Stewart,J.Comp.Chem.1989,10,209-220.
~([20b]) J.J.p.Stewart,J.Comp.Chem.1989,10,221-264.
[21]X.Zhang,Y.Zhang,J.Jiang,J.Mol.Struct.THEOCHEM,,2004,673,103-108.
[22]M.J.Frisch et al.,Gaussian-98,Revision A.9,Gaussian,Inc.,Pittsburgh PA,1998.
[23]SMART and SAINT for Windows NT Software Reference Manuals,Version 5.0,Bruker Analytical X-Ray Systems,Madison,WI,1997.
[24]G.M.Sheldrick,SADABS-A Software for Empirical Absorption Correction,University of G(o|¨)ttingen,1997.
[25]SHELXL Reference Manual,Version 5.1,Bruker Analytical X-Ray Systems,Madison,WI,1997.