含吡啶、咔唑基的ICT化合物的合成及光谱研究
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摘要
第一章：本章简要介绍了电荷转移化合物的分类、特点及应用,综述了电荷转移的研究进展和应用；吡啶及其衍生物的研究进展和应用；咔唑及其衍生物的研究进展和应用。
第二章：合成了CuI-Pyridine配合物,它是一种新型的固体荧光材料。测试了它的溶解性,采用IR、荧光等手段对其进行了表征。研究发现CuI-Pyridine呈非水溶性,固体状态下能发出强而稳定的黄色荧光(Emmax=577nm),但是溶解之后其荧光消失。
第三章：为了改善CuI-Pyridine配合物的物理性质,采用溶液搅拌法合成了CuI--Pyridine配合物与β-CD的包合物,用IR、1H NMR,荧光光谱等分析方法对其进行了表征,并用电分析方法初步研究了各种气体对此包合物修饰膜电极的响应。结果表明,CuI-Pyridine-β-CD为水溶性的荧光化合物(固体状态时Emmax=563nm),荧光发射稳定；CH4与CuI-Pyridine-β-CD发生竞争包合作用,随着CH4气体不断通入,包合物溶液的荧光强度逐渐降低。此外,CuI-Pyridine-β-CD包合物修饰膜电极对CH4气体有显著的响应。
第四章：以4-氨基吡啶为原料通过重氮化和碘代反应合成了4-碘代吡啶,然后与咔唑缩合合成了一种新型的具有发光性能的共轭化合物—N-吡啶基咔唑,再与CuI配体形成配合物。配合物及中间产物的结构经IR,1H NMR等测试得到初步证实,并对它们的荧光性质进行了初步研究以探讨结构与发光性能之间关系。由于在分子末端引入了咔唑基功能团,其荧光峰发生明显的红移(从365nm到424nm)且强度大大增强,为新型荧光化合物的研制开发和应用研究提供了理论基础。
第五章：合成了一种新型分子内电荷转移化合物(ICT)：三(N-乙基咔唑-3-基)甲醛缩2,4,7-三氨基芴酮(简称TECZFTAF),产物及中间体的结构经IR,1H NMR等表征。它是一种新型有机电荷传输化合物,将强供电子的咔唑基团与强吸电子的芴酮基团组装在同一个分子结构中,具有优良的电荷转移效果。并对其荧光性质进行了初步研究,最大激发波长为294nm,有两个最大发射峰：Emmax1=362nm、Emmax2=459nm。该化合物具有双发射峰,有望在未来光电子集成,生物分子探测,医学诊断,三维光信息存储,光动力学和双光子上转换激射等领域得到应用。
Chapter 1:The research progress and application of charge transfer were described in detail.The classification, characteristics and application of CTC, the recent development and application of pyridine derivatives, carbazole derivatives were reviewed briefly.
Chapter 2:Complex of CuI-Pyridine was synthesized and characterized by IR and fluorescence, and was a new solid fluorescent material.Its solubility was tested, and the luminescence properties of complex were studied. The results showed that CuI-Pyridine is non-water-soluble, which could emit strong and stable yellow fluorescence (Emmax=577nm) in solid state, but its fluorescence disappeared when complex was dissolved.
Chapter 3:To improve the physical properties of CuI-Pyridine, inclusion complex of CuI-Pyridine-β-CD was synthesized by solution mixing and characterized by IR、1H NMR and fluorescence, and the preliminary electrode response study between modified electrode and some gas have been done by the method of electrochemical analysis. The results showed that: CuI-Pyridine-β-CD was water-soluble, which could emit strong and stable fluorescence (Emmax=563nm in solid state), and its fluorescence could not disappear.The experiment revealed that there was competitive inclusion between CH4 and CuI-Pyridine-p-CD. With the addition of CH4, the fluorescence intensity of inclusion decrease gradually. Moreover, there was significant response between CH4 and CuI-Pyridine-β-CD modified electrode.
Chapter 4:4-Iodopyridine was synthesized by diazotization and iodine substitution with 4-amino-pyridine as the raw material, and then combined with carbazole to synthesize a new light-emitting dyes—N-Pyridyl carbazole. Finally, form complex with Cul.The structure of Complex and the intermediate product have confirmed by IR,1H NMR. We have studied their fluorescence properties and discussed the relations between structure and luminescence properties.Since the functional group of carbazole was introduced to the end of molecular, a red shift occurred from 365nm to 424nm and the fluorescent emission peak intensity was increased strongerly. It provided a theoretical basis of new fluorescent dyes's development and application.
Chapter 5:A new ICT compound:Tri(N-ethylycarbazole-3-yl) formolite-2,4,7-triaminofluorenone(TECzFTAF) has been designed and synthesized and confirmed by IR、1H NMR. Carbazole was a strong electron donor and fluorenone was a strong electron acceptor, carbazole group and fluorenone group were introduced into a molecule frame, a new organic charge-transfer compound was synthesized, which has an excellent charge-transfer effect. Its fluorescence properties were researched preliminarily, Exmax was at 294nm, Emmax was at 362nm or 459nm. In the future, the two emission peak of this compounds will be expected a strong application potential in the area of photoelectron integration, detection of biological molecules, diagnosis of medical, three-dimensional optical information storage, dynamics of optical and the conversion of excitation and emission in two-photon.
第二章：合成了CuI-Pyridine配合物,它是一种新型的固体荧光材料。测试了它的溶解性,采用IR、荧光等手段对其进行了表征。研究发现CuI-Pyridine呈非水溶性,固体状态下能发出强而稳定的黄色荧光(Emmax=577nm),但是溶解之后其荧光消失。
第三章：为了改善CuI-Pyridine配合物的物理性质,采用溶液搅拌法合成了CuI--Pyridine配合物与β-CD的包合物,用IR、1H NMR,荧光光谱等分析方法对其进行了表征,并用电分析方法初步研究了各种气体对此包合物修饰膜电极的响应。结果表明,CuI-Pyridine-β-CD为水溶性的荧光化合物(固体状态时Emmax=563nm),荧光发射稳定；CH4与CuI-Pyridine-β-CD发生竞争包合作用,随着CH4气体不断通入,包合物溶液的荧光强度逐渐降低。此外,CuI-Pyridine-β-CD包合物修饰膜电极对CH4气体有显著的响应。
第四章：以4-氨基吡啶为原料通过重氮化和碘代反应合成了4-碘代吡啶,然后与咔唑缩合合成了一种新型的具有发光性能的共轭化合物—N-吡啶基咔唑,再与CuI配体形成配合物。配合物及中间产物的结构经IR,1H NMR等测试得到初步证实,并对它们的荧光性质进行了初步研究以探讨结构与发光性能之间关系。由于在分子末端引入了咔唑基功能团,其荧光峰发生明显的红移(从365nm到424nm)且强度大大增强,为新型荧光化合物的研制开发和应用研究提供了理论基础。
第五章：合成了一种新型分子内电荷转移化合物(ICT)：三(N-乙基咔唑-3-基)甲醛缩2,4,7-三氨基芴酮(简称TECZFTAF),产物及中间体的结构经IR,1H NMR等表征。它是一种新型有机电荷传输化合物,将强供电子的咔唑基团与强吸电子的芴酮基团组装在同一个分子结构中,具有优良的电荷转移效果。并对其荧光性质进行了初步研究,最大激发波长为294nm,有两个最大发射峰：Emmax1=362nm、Emmax2=459nm。该化合物具有双发射峰,有望在未来光电子集成,生物分子探测,医学诊断,三维光信息存储,光动力学和双光子上转换激射等领域得到应用。
Chapter 1:The research progress and application of charge transfer were described in detail.The classification, characteristics and application of CTC, the recent development and application of pyridine derivatives, carbazole derivatives were reviewed briefly.
Chapter 2:Complex of CuI-Pyridine was synthesized and characterized by IR and fluorescence, and was a new solid fluorescent material.Its solubility was tested, and the luminescence properties of complex were studied. The results showed that CuI-Pyridine is non-water-soluble, which could emit strong and stable yellow fluorescence (Emmax=577nm) in solid state, but its fluorescence disappeared when complex was dissolved.
Chapter 3:To improve the physical properties of CuI-Pyridine, inclusion complex of CuI-Pyridine-β-CD was synthesized by solution mixing and characterized by IR、1H NMR and fluorescence, and the preliminary electrode response study between modified electrode and some gas have been done by the method of electrochemical analysis. The results showed that: CuI-Pyridine-β-CD was water-soluble, which could emit strong and stable fluorescence (Emmax=563nm in solid state), and its fluorescence could not disappear.The experiment revealed that there was competitive inclusion between CH4 and CuI-Pyridine-p-CD. With the addition of CH4, the fluorescence intensity of inclusion decrease gradually. Moreover, there was significant response between CH4 and CuI-Pyridine-β-CD modified electrode.
Chapter 4:4-Iodopyridine was synthesized by diazotization and iodine substitution with 4-amino-pyridine as the raw material, and then combined with carbazole to synthesize a new light-emitting dyes—N-Pyridyl carbazole. Finally, form complex with Cul.The structure of Complex and the intermediate product have confirmed by IR,1H NMR. We have studied their fluorescence properties and discussed the relations between structure and luminescence properties.Since the functional group of carbazole was introduced to the end of molecular, a red shift occurred from 365nm to 424nm and the fluorescent emission peak intensity was increased strongerly. It provided a theoretical basis of new fluorescent dyes's development and application.
Chapter 5:A new ICT compound:Tri(N-ethylycarbazole-3-yl) formolite-2,4,7-triaminofluorenone(TECzFTAF) has been designed and synthesized and confirmed by IR、1H NMR. Carbazole was a strong electron donor and fluorenone was a strong electron acceptor, carbazole group and fluorenone group were introduced into a molecule frame, a new organic charge-transfer compound was synthesized, which has an excellent charge-transfer effect. Its fluorescence properties were researched preliminarily, Exmax was at 294nm, Emmax was at 362nm or 459nm. In the future, the two emission peak of this compounds will be expected a strong application potential in the area of photoelectron integration, detection of biological molecules, diagnosis of medical, three-dimensional optical information storage, dynamics of optical and the conversion of excitation and emission in two-photon.
引文
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