氨基卟啉及其衍生物与环糊精的超分子体系研究
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摘要
卟啉及其金属配合物是细胞色素、血红素和叶绿素等生物体的必需物质,在生物学进展中起到了重要的作用。卟啉—CDs超分子体系的研究在基因免疫印迹分析、药物控制释放、手性识别、分子开关以及模拟酶等多个领域有着非常广泛的应用前景。卟啉—CDs的包结机理研究日臻完善,该领域的发展必将对生命科学、医药等方面的研究发展作出巨大的贡献。
本文合成了5-(4-硝基苯基)-10,15,20-三苯基卟啉(NTPPH2)和5-(4-氨基苯基)-10,15,20-三苯基卟啉(ATPPH2),对化合物进行了详细的表征并确认了其结构。利用荧光光谱法、紫外—可见分光光度法研究了NTPPH2、ATPPH2分别与α-CD、β-CD和γ-CD形成的超分子体系,测定了六种包结物的包结常数和包结比,探讨了推电子基团和吸电子基团对包结过程的影响,结果表明推电子基团更有利于包结物的形成。
设计合成了一种未见文献报道新型卟啉5-(4-苯甲酰亚胺基苯基)-10,15,20-三苯基卟啉(BATPPH2)及其Zn配合物(BATPPZn),对化合物进行了详细的表征并确认了其结构。利用荧光光谱法、紫外—可见分光光度法和1H NMR技术研究了BATPPH2以及BATPPZn与不同空腔大小的环糊精形成的超分子体系。研究结果表明BATPPH2和BATPPZn尺寸、几何形状与γ-CD的空腔尺寸和性质更为匹配;Zn2+的配位作用使包结物的稳定性降低,但对包结物的包结比并没有产生很大影响。
合成了一系列不同取代位置和不同官能团数目的氨基卟啉:5-(4-氨基苯基)-10,15,20-三苯基卟啉(ATPPH2)、5,10-二(4-氨基苯基)-15,20-二苯基卟啉(Cis-DADPPH2)、5,15-二(4-氨基苯基)-10,20-二苯基卟啉(Trans-DADPPH2)、5-苯基-10,15,20-三(4-氨基苯基)卟啉(Tri-APPH2)以及四(4-氨基苯基)卟啉(TAPPH2),对化合物进行了详细的表征并确认了其结构。研究了其与环糊精(α-CD、β-CD和γ-CD)超分子体系,探讨了不同数目及不同位置的氨基官能团对包结的影响。结果表明二氨基苯基取代卟啉对位取代(5, 15位)比邻位取代(5, 10位)更有利于与α-CD、β-CD和γ-CD形成稳定、单一的包结物;氨基官能团数目对包结过程产生了一定的影响,其数目的增加有利于包结过程稳定、有序的进行。确定了所有包结物的相关系数,寻找其规律并探讨了其作用机理,联系生命科学寻求其应用的可能性。该系列超分子体系研究具有系统性,在系列性、系统性研究中寻找规律,理论意义较强。
Porphyrin and it’s metal complexes are the requisite substances of cytochrome, hemachrome, chlorophyll, etc, which play significant roles in biological processes. The research of Cyclodextrin-Porphyrin supramolecular system had been widely used in the field of blot analysis of genes, drug controlled releasing, chiral recognition, molecular switches and analog enzyme. Porphyrin-CD’s inclusion mechanism is perfected daily, and the field's development is very contributing to the progress of life science and pharmaceutical research.
In this thesis, NTPPH2 and ATPPH2 were synthesized and characterized. And the supramolecular system of the porphyrins withα-CD,β-CD andγ-CD were studied in detail by means of fluorescence spectroscopy and UV-visible spectrophotometry. Determined the formation constants of the six supramolecular systems.We discussed the effect of electron-donating group and electron-withdrawing group on inclusion. The results show that the electron-donating group is more conducive to the formation of inclusion.
We also synthesized BATPPH2 and its Zn complexes, verified their structure. Studied on the supramolecular system of BATPPH2 and BATPPZn with different cavity size of cyclodextrin by fluorescence spectroscopy, UV-vis, and 1H NMR. Investigated the effect that Zn2+ of the porphyrin ring plays on the process of inclusion. The results show that the size of BATPPH2 and BATPPZn matches with the cavity size ofγ-CD best; Zn2+ strongly impeded the process of inclusion, but hardly impact the ratio of complex.
A series of amino porphyrin with different substituted position (Cis-DADPPH2, Trans-DADPPH2, Tri-APPH2 and TAPPH2) were synthesized, and their structure were confirmed. Studied on their supramolecular system with different cyclodextrins, and researched into the influence of position and the number of amino groups on inclusion, try to find the law and explore its inclusion mechanism. As this series are very systematic, they will have considerably theoretical significance. All of the research have not been reported.
本文合成了5-(4-硝基苯基)-10,15,20-三苯基卟啉(NTPPH2)和5-(4-氨基苯基)-10,15,20-三苯基卟啉(ATPPH2),对化合物进行了详细的表征并确认了其结构。利用荧光光谱法、紫外—可见分光光度法研究了NTPPH2、ATPPH2分别与α-CD、β-CD和γ-CD形成的超分子体系,测定了六种包结物的包结常数和包结比,探讨了推电子基团和吸电子基团对包结过程的影响,结果表明推电子基团更有利于包结物的形成。
设计合成了一种未见文献报道新型卟啉5-(4-苯甲酰亚胺基苯基)-10,15,20-三苯基卟啉(BATPPH2)及其Zn配合物(BATPPZn),对化合物进行了详细的表征并确认了其结构。利用荧光光谱法、紫外—可见分光光度法和1H NMR技术研究了BATPPH2以及BATPPZn与不同空腔大小的环糊精形成的超分子体系。研究结果表明BATPPH2和BATPPZn尺寸、几何形状与γ-CD的空腔尺寸和性质更为匹配;Zn2+的配位作用使包结物的稳定性降低,但对包结物的包结比并没有产生很大影响。
合成了一系列不同取代位置和不同官能团数目的氨基卟啉:5-(4-氨基苯基)-10,15,20-三苯基卟啉(ATPPH2)、5,10-二(4-氨基苯基)-15,20-二苯基卟啉(Cis-DADPPH2)、5,15-二(4-氨基苯基)-10,20-二苯基卟啉(Trans-DADPPH2)、5-苯基-10,15,20-三(4-氨基苯基)卟啉(Tri-APPH2)以及四(4-氨基苯基)卟啉(TAPPH2),对化合物进行了详细的表征并确认了其结构。研究了其与环糊精(α-CD、β-CD和γ-CD)超分子体系,探讨了不同数目及不同位置的氨基官能团对包结的影响。结果表明二氨基苯基取代卟啉对位取代(5, 15位)比邻位取代(5, 10位)更有利于与α-CD、β-CD和γ-CD形成稳定、单一的包结物;氨基官能团数目对包结过程产生了一定的影响,其数目的增加有利于包结过程稳定、有序的进行。确定了所有包结物的相关系数,寻找其规律并探讨了其作用机理,联系生命科学寻求其应用的可能性。该系列超分子体系研究具有系统性,在系列性、系统性研究中寻找规律,理论意义较强。
Porphyrin and it’s metal complexes are the requisite substances of cytochrome, hemachrome, chlorophyll, etc, which play significant roles in biological processes. The research of Cyclodextrin-Porphyrin supramolecular system had been widely used in the field of blot analysis of genes, drug controlled releasing, chiral recognition, molecular switches and analog enzyme. Porphyrin-CD’s inclusion mechanism is perfected daily, and the field's development is very contributing to the progress of life science and pharmaceutical research.
In this thesis, NTPPH2 and ATPPH2 were synthesized and characterized. And the supramolecular system of the porphyrins withα-CD,β-CD andγ-CD were studied in detail by means of fluorescence spectroscopy and UV-visible spectrophotometry. Determined the formation constants of the six supramolecular systems.We discussed the effect of electron-donating group and electron-withdrawing group on inclusion. The results show that the electron-donating group is more conducive to the formation of inclusion.
We also synthesized BATPPH2 and its Zn complexes, verified their structure. Studied on the supramolecular system of BATPPH2 and BATPPZn with different cavity size of cyclodextrin by fluorescence spectroscopy, UV-vis, and 1H NMR. Investigated the effect that Zn2+ of the porphyrin ring plays on the process of inclusion. The results show that the size of BATPPH2 and BATPPZn matches with the cavity size ofγ-CD best; Zn2+ strongly impeded the process of inclusion, but hardly impact the ratio of complex.
A series of amino porphyrin with different substituted position (Cis-DADPPH2, Trans-DADPPH2, Tri-APPH2 and TAPPH2) were synthesized, and their structure were confirmed. Studied on their supramolecular system with different cyclodextrins, and researched into the influence of position and the number of amino groups on inclusion, try to find the law and explore its inclusion mechanism. As this series are very systematic, they will have considerably theoretical significance. All of the research have not been reported.
引文
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