功能化金属—有机大环的组装及应用
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摘要
超分子化学的研究范围是由两个或更多的化学实体通过分子间弱相互作用而构建的高度有序及复杂性的体系。通过主客体之间的弱相互作用引起主体结构的变化,是分子识别,多相／均相催化的理论基础。金属-有机大环结构是一类人工合成的,旨在模拟和学习酶催化及识别过程的重要模型。在均相体系中,金属-有机大环结构的空腔不仅有利于对特定底物分子的选择性识别；同时还可以通过非共价弱相互作用将不同的底物分子限定在其中特定的区域、进而选择性的催化某些特定反应的进行,体现出纳米微反应器的功能。以具有高对称性及有机活性位点的金属-有机大环作为构筑模块、在不同溶剂或模板的作用下通过空间堆积、可以得到具有不同孔道结构的微孔分子材料,进而可以在非均相体系中对某些特定的底物分子进行选择性的吸附与包合,从而体现出选择性催化功能。本论文包含以下几方面研究内容：
1.基于酰胺基团的金属-有机大环的组装及其对核苷、氨基葡萄糖的选择性识别：以具有良好发光性能及配位活性的喹啉基团作为配位基团及荧光信号输出单元、以酰胺基团作为氢键识别位点、合成了L1、L3和L4三种配体,通过与具有平面四配位构型的Pd2+进行组装,分别得到了正八面体构型的大环化合物CA1、以及三角形大环CA3和CA4。模拟酶的识别过程,通过酰胺基团与尿苷和氨基葡萄糖之间较强的互补型氢键、在CA1中实现了对尿苷和氨基葡萄糖分子的选择性荧光识别；同时在CA3中实现了对尿苷的选择性识别；在CA4中,作为给电子基团的柔性烷氧基团的引入使得该大环化合物对于胞苷具有选择性识别功能,并且胞苷与CA4之间的互补型氢键对于CA4的组装与反组装具有导向作用,因而实现了对不同生物分子的选择性识别。
2.金属-有机大环为构筑模块的微孔分子材料在非均相催化中的应用：在柔性适中的四单齿配体L2中引入了具有氢键作用位点及弱碱催化性能的酰胺基团,在不同模板作用下与具有平面四配位构型的Pd2+进行组装,得到了以三元金属-有机大环作为构筑模块、具有不同孔道结构的微孔分子材料CA2、CA6。不同的孔道结构赋予了其不同的催化性能,其中CA2在非均相体系中对Knoevenagel缩合反应体现出了很好的尺寸选择性催化功能。在配体中引入柔性基团,考察了配体L5的柔性对于金属-有机大环结构稳定性的影响；研究了由L5与Pd2+组装得到的金属-有机大环结构CA7在溶液中的稳定性以及解离与重组过程。通过含有氨基活性基团的多齿席夫碱配体L6与具有平面四配位构型的Ni2+进行自组装得到了配体与金属节点的化学计量比为4：4的金属-有机大环CA8。该大环结构通过氨基与亚氨基之间的氢键作用、分子之间的p-p堆积作用形成了含有二维层状网络以及—围孔道的结构,同时多孔结构的特性使得该微孔分子材料对Knoevenagel缩合反应具有很好的尺寸选择性催化功能。
3.正四面体金属-有机大环的组装及其在均相催化方面的应用：通过含有大的p共轭基团的三双齿席夫碱配体与正八面体配位构型的过渡金属离子Zn2+、Cd2+及Co2+进行组装得到了一系列具有正四面体孔穴结构的金属-有机大环化合物CA9、CA10及CA11,并通过荧光分析的方法研究了其主客体化学行为。含有正电荷的四面体大环化合物可通过静电作用、p-p堆积作用将两个具有大共轭基团的anthracene-9-carboxylicacid客体包合在其空腔内部特定的区域,催化其进行自身的二聚反应,体现出纳米微反应器功能。
The study field of supramolecular chemistry is high-order and complicated system constituted from two or more moleculars through weak interaction between different molecules. The weak interaction between host and guest could lead to the structure changing of host and is the base of molecule recognition and heterogeneous/homogeneous catalysis. Synthetic and functional metal-organic macrocycles are important models to realize the process of enzyme catalysis and recognition. In homogeneous system, these cavity-containing compounds can encapsulate and stabilize guest substrates through weak interaction with selective signal response and chemical transformations can be catalyzed within these "microreactor". Using the metal-organic macrocycles having high symmetry and organic active sites as building blocks, microporous molecular materials packed with different type of cavities could be obtained in presence of different solvents or templates. These materials would adsorb and encapsulate some special substrates, display the advantages of heterogeneous catalysis. The present paper contains following several aspects:
1. Self-assembly of metal-organic macrocycles containing amide groups as active sites and their applications in the sensor of nucleoside and glucosamine:Quinoline groups in the well-moderated ligands act as both the fluorophore units and parts of the coordination sites, and the amide groups as hydrogen bonding triggers for guest molecules, a truncated octahedral and two triangle metal-organic macrocycles (CA1、CA3 and CA4) have been assemblied using three mono-dentate ligands (L1、L3 and L4) incorporating with Pd2+. CA1 and CA3 have achieved selective fluorescent detection for uridine because of the two-fold complementary hydrogen-bonding between uridine and amide is stronger than that of the other three riboneclosides, CA1 had also demonstrated fluorescent response for glucosamine. In present of flexible chain acted as electronic-donor, CA4 demonstrated selective fluorescent detection for cytidine. Furthermore, the hydrogen-bonding between cytidine and CA4 could induce disassociation and recomposition process of CA4 so as to realize selective recognition for different bio-molecular.
2. Microporous molecular materials containing metal-organic macrocycles as building blocks and their applications in heterogeneous catalysis:Upon introducing the multiple amide groups into a proper-flexible tetra-monodentate ligand (L2) as hydrogen bonding and weak-base catalysis actived sites, we have obtained two microporous molecular materials (CA2 and CA6) having different cavities in present of different solvents or templates. CA2 demonstrated size-selective catalysis for Knoevenagel condensation reaction in heterogeneous system. Upon introducing a flexible chain into the ligand (L5) containing tetra-monodentate binding sites, we have studied the effection of the flexible ligand for the stability and recombinational prccess of CA7 assembled from L5 and Pd2+ in solution. A quadrangle macrocycle (CA8) has been obtained using multi-dentate ligand (L6) and Ni2+. This tetramer has amino groups as guest interaction and weak-base catalysis actived sites. The hydrogen bond between amino and imine group and p-p interaction in different tetramer lead to 2D network and 1D channel in the crystal structure of CA8. CA8 demonstrated size-selective catalysis for Knoevenagel condensation reaction in heterogeneous system.
3. Self-assembly of tetrahedral metal-organic cycles and their application in homogeneus catalysis:a serious of new molecular tetrahedrons (CA9、CA10、CA11) were prepared via self-assembly between Zn2+、Cd2+、Co2+and tri-dimdentate schiff-base ligand (L7) containing large aromatic and conjugated group as p-p interaction sites. Host-guest complexation behaviour between the tetrahedron compound and anthracene-9-carboxylicacid was investigated using the methord of fluorometry titration. The cation tetrahedron host could encapsulate two anthracene-9-carboxylicacid vis static and p-p interaction, and the selective photodimerization reaction of typically unreactive substrates was engineered using a self-assembled molecular falsk. The molecular tetrahedron brang the reactions in close proximity、fixed their relative orientations within the restrictive cavity and demonstrated the ability of microreactor.
1.基于酰胺基团的金属-有机大环的组装及其对核苷、氨基葡萄糖的选择性识别：以具有良好发光性能及配位活性的喹啉基团作为配位基团及荧光信号输出单元、以酰胺基团作为氢键识别位点、合成了L1、L3和L4三种配体,通过与具有平面四配位构型的Pd2+进行组装,分别得到了正八面体构型的大环化合物CA1、以及三角形大环CA3和CA4。模拟酶的识别过程,通过酰胺基团与尿苷和氨基葡萄糖之间较强的互补型氢键、在CA1中实现了对尿苷和氨基葡萄糖分子的选择性荧光识别；同时在CA3中实现了对尿苷的选择性识别；在CA4中,作为给电子基团的柔性烷氧基团的引入使得该大环化合物对于胞苷具有选择性识别功能,并且胞苷与CA4之间的互补型氢键对于CA4的组装与反组装具有导向作用,因而实现了对不同生物分子的选择性识别。
2.金属-有机大环为构筑模块的微孔分子材料在非均相催化中的应用：在柔性适中的四单齿配体L2中引入了具有氢键作用位点及弱碱催化性能的酰胺基团,在不同模板作用下与具有平面四配位构型的Pd2+进行组装,得到了以三元金属-有机大环作为构筑模块、具有不同孔道结构的微孔分子材料CA2、CA6。不同的孔道结构赋予了其不同的催化性能,其中CA2在非均相体系中对Knoevenagel缩合反应体现出了很好的尺寸选择性催化功能。在配体中引入柔性基团,考察了配体L5的柔性对于金属-有机大环结构稳定性的影响；研究了由L5与Pd2+组装得到的金属-有机大环结构CA7在溶液中的稳定性以及解离与重组过程。通过含有氨基活性基团的多齿席夫碱配体L6与具有平面四配位构型的Ni2+进行自组装得到了配体与金属节点的化学计量比为4：4的金属-有机大环CA8。该大环结构通过氨基与亚氨基之间的氢键作用、分子之间的p-p堆积作用形成了含有二维层状网络以及—围孔道的结构,同时多孔结构的特性使得该微孔分子材料对Knoevenagel缩合反应具有很好的尺寸选择性催化功能。
3.正四面体金属-有机大环的组装及其在均相催化方面的应用：通过含有大的p共轭基团的三双齿席夫碱配体与正八面体配位构型的过渡金属离子Zn2+、Cd2+及Co2+进行组装得到了一系列具有正四面体孔穴结构的金属-有机大环化合物CA9、CA10及CA11,并通过荧光分析的方法研究了其主客体化学行为。含有正电荷的四面体大环化合物可通过静电作用、p-p堆积作用将两个具有大共轭基团的anthracene-9-carboxylicacid客体包合在其空腔内部特定的区域,催化其进行自身的二聚反应,体现出纳米微反应器功能。
The study field of supramolecular chemistry is high-order and complicated system constituted from two or more moleculars through weak interaction between different molecules. The weak interaction between host and guest could lead to the structure changing of host and is the base of molecule recognition and heterogeneous/homogeneous catalysis. Synthetic and functional metal-organic macrocycles are important models to realize the process of enzyme catalysis and recognition. In homogeneous system, these cavity-containing compounds can encapsulate and stabilize guest substrates through weak interaction with selective signal response and chemical transformations can be catalyzed within these "microreactor". Using the metal-organic macrocycles having high symmetry and organic active sites as building blocks, microporous molecular materials packed with different type of cavities could be obtained in presence of different solvents or templates. These materials would adsorb and encapsulate some special substrates, display the advantages of heterogeneous catalysis. The present paper contains following several aspects:
1. Self-assembly of metal-organic macrocycles containing amide groups as active sites and their applications in the sensor of nucleoside and glucosamine:Quinoline groups in the well-moderated ligands act as both the fluorophore units and parts of the coordination sites, and the amide groups as hydrogen bonding triggers for guest molecules, a truncated octahedral and two triangle metal-organic macrocycles (CA1、CA3 and CA4) have been assemblied using three mono-dentate ligands (L1、L3 and L4) incorporating with Pd2+. CA1 and CA3 have achieved selective fluorescent detection for uridine because of the two-fold complementary hydrogen-bonding between uridine and amide is stronger than that of the other three riboneclosides, CA1 had also demonstrated fluorescent response for glucosamine. In present of flexible chain acted as electronic-donor, CA4 demonstrated selective fluorescent detection for cytidine. Furthermore, the hydrogen-bonding between cytidine and CA4 could induce disassociation and recomposition process of CA4 so as to realize selective recognition for different bio-molecular.
2. Microporous molecular materials containing metal-organic macrocycles as building blocks and their applications in heterogeneous catalysis:Upon introducing the multiple amide groups into a proper-flexible tetra-monodentate ligand (L2) as hydrogen bonding and weak-base catalysis actived sites, we have obtained two microporous molecular materials (CA2 and CA6) having different cavities in present of different solvents or templates. CA2 demonstrated size-selective catalysis for Knoevenagel condensation reaction in heterogeneous system. Upon introducing a flexible chain into the ligand (L5) containing tetra-monodentate binding sites, we have studied the effection of the flexible ligand for the stability and recombinational prccess of CA7 assembled from L5 and Pd2+ in solution. A quadrangle macrocycle (CA8) has been obtained using multi-dentate ligand (L6) and Ni2+. This tetramer has amino groups as guest interaction and weak-base catalysis actived sites. The hydrogen bond between amino and imine group and p-p interaction in different tetramer lead to 2D network and 1D channel in the crystal structure of CA8. CA8 demonstrated size-selective catalysis for Knoevenagel condensation reaction in heterogeneous system.
3. Self-assembly of tetrahedral metal-organic cycles and their application in homogeneus catalysis:a serious of new molecular tetrahedrons (CA9、CA10、CA11) were prepared via self-assembly between Zn2+、Cd2+、Co2+and tri-dimdentate schiff-base ligand (L7) containing large aromatic and conjugated group as p-p interaction sites. Host-guest complexation behaviour between the tetrahedron compound and anthracene-9-carboxylicacid was investigated using the methord of fluorometry titration. The cation tetrahedron host could encapsulate two anthracene-9-carboxylicacid vis static and p-p interaction, and the selective photodimerization reaction of typically unreactive substrates was engineered using a self-assembled molecular falsk. The molecular tetrahedron brang the reactions in close proximity、fixed their relative orientations within the restrictive cavity and demonstrated the ability of microreactor.
引文
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