含氟二芳烯构筑的光控离子传输“通道”
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摘要
由于光致变色二芳烯材料具有很高的光致关环/开环效率,很好的抗疲劳性,两种异构体都有良好的热稳定性,在光电器件和分子开关具有潜在的应用价值。在可见光和紫外光照射下二芳烯分子具有两种不同的异构体,可以利用这两种结构构筑两种不同形貌的超分子体系,这两种自组装的超分子结构通过光致形貌变化来影响离子“通道”的有序性,达到调节离子的传输的目的。
论文的第一部分合成了三种二芳烯化生物,其中两种是新型的二芳烯化合物,这些化合物都具有优良的光致变色性能,论文的第二部分则研究了这些化合物在溶液中的光致变色性质。
论文的第三部分用紫外-可见吸收光谱,动态光散射,扫描电子显微镜,透射电子显微镜和原子力显微镜等技术研究了这些化合物在不同的光照条件下的自组装性能。含组胺侧链的二芳烯在紫外光照射下自组装结构从纳米纤维转化成了纳米小球,而且pH值对自组装结构具有很大的影响,增大pH值更利于自组装结构的形成,通过理论计算研究了这个化合物可能的自组装,同时做了这个化合物在微电极上的交流阻抗来说明用二芳烯自组装超分子结构构筑光控离子通道的可行性。
Diarylethenes have shown great promise as new materials for optoelectronic devices and molecular switches due to a high conversion efficiency of reversible photochromic reactivity, excellent thermal stability of both isomers and good fatigue resistance. The diarylethene derivatives have two isomers under the irradiation of the visible and ultraviolet, two supramolecular structures can be built by the two different morphologies.the order of the Ion "channel”can change by the morphologies of the two supramolecular structures to achieve the purpose of regulating ion transport.
In the present dissertation, three diarylethene compounds were synthesized, two of which were synthesized for the first time. As novel photoelectrochromic materials, the compounds have special properties. The charactertistic photochemical and photophysical properties in solutions were researched in the second part of the dissertation.
In the third part, the self-assembling behavior of the three diarylethene derivatives originating from photochromic conformation tuned by photo irradiation was investigated using UV-Vis absorption spectra, dynamic light scattering, scanning electron microscopy and atomic force microscopy techniques. For the diarylethene derivatives with histamine side chains it is surprising to find that the morphology of super molecular architectures was tuned from nanofibers into spherical nanoparticles by photo irradiation. It was also revealed that the corresponding architectures are closely dependant on pH values of the aqueous solution, which indicate there is a great possibility that the increasing pH values are favourable for rigid aggregates. The theoretic calculations and models of the self-assembled nanostructure were presented to illuminate the possible self-assemble mechanism. Electrochemical Impedance Spectroscopy in the micro-electrode was done to illustrate the feasibility of building ion channels by diarylethene derivatives.
论文的第一部分合成了三种二芳烯化生物,其中两种是新型的二芳烯化合物,这些化合物都具有优良的光致变色性能,论文的第二部分则研究了这些化合物在溶液中的光致变色性质。
论文的第三部分用紫外-可见吸收光谱,动态光散射,扫描电子显微镜,透射电子显微镜和原子力显微镜等技术研究了这些化合物在不同的光照条件下的自组装性能。含组胺侧链的二芳烯在紫外光照射下自组装结构从纳米纤维转化成了纳米小球,而且pH值对自组装结构具有很大的影响,增大pH值更利于自组装结构的形成,通过理论计算研究了这个化合物可能的自组装,同时做了这个化合物在微电极上的交流阻抗来说明用二芳烯自组装超分子结构构筑光控离子通道的可行性。
Diarylethenes have shown great promise as new materials for optoelectronic devices and molecular switches due to a high conversion efficiency of reversible photochromic reactivity, excellent thermal stability of both isomers and good fatigue resistance. The diarylethene derivatives have two isomers under the irradiation of the visible and ultraviolet, two supramolecular structures can be built by the two different morphologies.the order of the Ion "channel”can change by the morphologies of the two supramolecular structures to achieve the purpose of regulating ion transport.
In the present dissertation, three diarylethene compounds were synthesized, two of which were synthesized for the first time. As novel photoelectrochromic materials, the compounds have special properties. The charactertistic photochemical and photophysical properties in solutions were researched in the second part of the dissertation.
In the third part, the self-assembling behavior of the three diarylethene derivatives originating from photochromic conformation tuned by photo irradiation was investigated using UV-Vis absorption spectra, dynamic light scattering, scanning electron microscopy and atomic force microscopy techniques. For the diarylethene derivatives with histamine side chains it is surprising to find that the morphology of super molecular architectures was tuned from nanofibers into spherical nanoparticles by photo irradiation. It was also revealed that the corresponding architectures are closely dependant on pH values of the aqueous solution, which indicate there is a great possibility that the increasing pH values are favourable for rigid aggregates. The theoretic calculations and models of the self-assembled nanostructure were presented to illuminate the possible self-assemble mechanism. Electrochemical Impedance Spectroscopy in the micro-electrode was done to illustrate the feasibility of building ion channels by diarylethene derivatives.
引文
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[11] Tian H, Yang S J. Recent progresses on diarylethene based photochromic switches [J]. Chem. Soc. Rev., 2004, 33(2): 85~97.
[12] Morimitsu K, Kobatake S, Irie M. Large geometrical structure changes of photochromic diarylethenes upon photoirradiation [J]. Tetrahedron., Lett. 2004, 45(6): 1155~1158.
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[39]缪文娟,含五-六元环骨架的新型二芳烯分子合成及性质研究, [学位论文]江西科技师范学院:江西科技师范学院,2010
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[2]干福熹.光子学材料及其发展[J].材料科学与工程,1998,16(2):1~8
[3] Borg H J, Woudenberg R. Trends in optical recording [J]. Journal of Magnetism and Magnetic Materials., 1999, 193: 519~525
[4] Gan F, Hou L, Wang G, et al. Optical and recording properties of short wavelength optical storage materials [J]. Materials Science & Engineering., 2000, B76: 63~68
[5] Mccormick F B, Zhang H, Dvornikov A, et al. Parallel access 3-D multilayer optical storage using 2-photon recording [J]. SPIE., 1999, 3802: 173~181
[6] Hunter S, Kiamilev F, Esener S, et al. Potentials of two-photon based 3-D optical memories for high performance computing [J]. Applied Optics., 1990, 29: 2058~2066
[7] Parthenopoulos D A and Rentzepis P M. Three-dimensional optical storage memory [J]. Science., 1989, 245: 843~845
[8] Irie M, Mohri M. Thermally irreversible photochromic systems.Reversible photocyclization of diarylethene derivatives [J]. J. Org. Chem., 1988, 53(4): 803~808.
[9] Gilat S L, Kawai S H, Lehn J M. Light-triggered electrical and optical switching devices [J]. J. Chem. Soc. Chem. Commun. 1993, 18: 1439~1442.
[10] Irie M. Diarylethenes for memories and switches [J]. Chem. Rev., 2000, 100(5): 1685~1716.
[11] Tian H, Yang S J. Recent progresses on diarylethene based photochromic switches [J]. Chem. Soc. Rev., 2004, 33(2): 85~97.
[12] Morimitsu K, Kobatake S, Irie M. Large geometrical structure changes of photochromic diarylethenes upon photoirradiation [J]. Tetrahedron., Lett. 2004, 45(6): 1155~1158.
[13] Feringa B L. Molecular Switches. Weinheim: Wiley-VCH., 2001.
[14] Matsuda K, Irie M. Diarylethene as a photoswitching unit [J]. J.Photochem. Photobiol, C: Photochem. Rev., 2004, 5(2): 169~182.
[15] Raymo F M, Tomasulo M. Electron and energy transfer modulation with photochromic switches [J]. Chem. Soc. Rev., 2005, 34(4): 327~336.
[16] Wang S, Shen W, Feng Y L, Tian H. A multiple switching bisthienylethene and its photochromic fluorescent organogelator [J]. Chem. Commun., 2006, 14: 1497~1499.
[17] Zhou Z G, Xiao S Z, Xu J, Liu Z, Shi M, Li F, Yi T, Huang C. Modulation of photochromic property in an organoboron-based diarylethene by fluoride ion [J]. Org. Lett., 2006, 8(18): 3911~3914.
[18] Zhou Z G, Yang H, Shi M, Xiao S Z, Li F Y, Yi T, Huang C H. Photochromic organoboron-based dithienylcyclopentene modulated by fluoride and mercuric(II)ions [J]. Chem. Phys. Chem.,2007, 8(9): 1289~1292.
[19] Lien L, Jaikaran D, Zhang Z, Woolley G. Photomodulated blocking of gramicidin ion channels [J]. J. Am. Chem. Soc., 1996, 118: 12222~12223.
[20] Ueda T, Nagamine K, Kimura S, Imanishi Y. Photoresponsive melittin having a spyropyran residue in the hydrophobic region of the sequence [J]. J. Chem. Soc., Perkin Trans., 1995, 2: 365~368.
[21] Anzai J, Osa T. Electrochemical and optical properties of an azo dye based conducting copolymer [J]. Tetrahedron., 1994, 50: 4039~4070.
[22] Talukdar P, Bollot G, Mareda J, Sakai N, Matile S. Synthetic ion channels with rigid-rod p-stack architecture that open in response to chargetransfer complex formation [J]. J. Am. Chem. Soc., 2005, 127: 6528~6529.
[23] Watt G, Kotz J, Sheppard T L. Ion channels get flashy [J]. Nature Chem. Biology., 2006, 2(1): 11~13.
[24] Lien L, Jaikaran D, Zhang Z, Woolley G. Photomodulated blocking of gramicidin ion channels [J]. J. Am. Chem. Soc., 1996, 118: 12222~12223.
[25] Irie M, Mohri M.Thermally Irreversible Photochromic Systems. Reversible Photocyclization of Diarylethene Derivatives [J]. J. Org. Chem., 1988, 53: 803~808
[26]钟少锋,涂海洋.有机光存储材料二芳乙烯化合物研究的进展[J].感光科学与光化学. 2003, 21(3): 200~211
[27] Nakamura S, Irie M. Thermally irreveraible photochromic systems. A theoretical study [J]. J. Org. Chem., 1988, 53: 6136~6138
[28] Tsujioka T, Kume M, Irie M. Photochromic reactions of a diarylthene derivative in polymer matrices [J]. Journal of photochemistry and photobiology A: chemistry., 1997, 104: 203~206
[29] Irie M, Lifka T, Kobatake S, et al. Photochromism of 1,2-bis(2-methyl-5-phenyl-3- thienyl)perfluorocyclopentene in a single-crystalline phase [J]. J. Am. Chem. Soc., 2000, 122, 4871~4876
[30]黄震年,赵伟力,樊美公.光存储用有机光致变色新材料-二芳杂环基乙烯化合物研究概况[J] .化学通报. 1996, 12: 16~22
[31]钟少锋,涂海洋,有机光存储材料二芳乙烯化合物研究的进展.感光科学与光化学[J]. 2003, 21(3): 200~211
[32] Irie M, Miyatake O, Uchida K. Blocked photochromism of diarylethenes [J]. J. Am. Chem. Soc., 1992, 114: 8715~8716
[33] Kawai S H, Gilat S L, Lehn J M. Photochemical pKa-modulation and gated photochromic properties of a novel diarylethene switch [J]. Eur. J. Org. Chem., 1999: 2359~2366
[34] Young A J, Frank H A. Energy transfer reactions involving carotenoids: quenching of chlorophyll fluorescence [J]. J .Photochem. Photobiol .B: Biol., 1996, 36: 3215
[35] Gillbro T, Anderson R S, Liu R S, et al. Location of the carotenoid 2Ag-state and its role in photosynthesis [J]. Photochem. Photobiol., 1993, 57: 44~48
[36] Miyasaka H, Nobuto T, Jiayal A, et al. Picosecond laser photolysis studies on a photo- chromic dithienylethene in solution and in crystalline phases [J]. Chem. Phys. Lett., 1997, 269: 281~285
[37] Irie M, Eriguchi T, Takada T, et al. Phtochromism of diarylethenes having thiophene oligomers as the aryl groups [J]. Tetrahedron., 1997, 53: 12263~12271
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