5-芳基-1，3，4-噁二唑衍生物分子的合成及其荧光性质研究
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摘要
本论文设计并合成了几种5-芳基-1,3,4-噁二唑作为骨架部分的共轭配体,分别对金属离子的荧光响应、稀土配合物和有机小分子器件三个方面进行了研究。主要内容包括：
第一章,简单介绍了荧光传感器和稀土配合物的研究背景和应用,重点介绍了Zn2+荧光传感器的配体分类和研究现状、稀土配合物的机理和设计
第二章,设计和合成了一种芳基-1,3,4-噁二唑类衍生物的荧光传感器。Zn2+离子通过亲电进攻,有效地与酚羟基上富含电子的氧原子结合,形成的金属配合物刚性平面结构可以阻止2-羟基-苯基-1,3,4-噁二唑中的二个芳香基团的扭转运动,抑制了金属诱导的无辐射跃迁,从而在水溶液中发出了亮蓝色荧光。我们成功地将该传感器L1应用于生物活细胞中,通过荧光共聚焦显微镜技术,实现了对肝癌细胞中高Zn2+离子浓度的荧光成像检测分析；
第三章,设计并合成了两种5-芳基-1,3,4-噁二唑类衍生物为骨架的酰胺型配体,考察该类配体骨架共轭结构能否有效敏化稀土配合物的特征荧光,并通过对苯环上官能团的取代,初步研究存在的羟基和芳香基团的扭转运动对稀土配合物固液状态下荧光的影响；
第四章,设计和合成了三个以5-芳基-1,3,4嗯二唑为主体的有机分子,并通过核磁和荧光光谱表征了这些化合物。荧光分析表明这些有机化合物在溶液中显示出弱的荧光,而在固态下表现出较强的亮蓝色荧光,从而避免了有机分子的浓度淬灭效应。我们将其中一个有机化合物蒸空镀膜制备成有机发光半导体器件,并对该器件进行了电致发光测试。
In this thesis, we have designed and synthesized some different5-aryl-1,3,4-oxadiazole-based ligands. The fluorescence response of L1to the metal ions, rare earth complexes of L2/L3and organic molecules devices prepared by Pox-1have also been investigated, respectively. The main contents including:
In the first section, we briefly describe the background and application of fluorescent chemosensors and the rare earth complexes. We especially focus on the classification of fluorescent sensors for zinc ion and design of rare earth complexes.
In the second section, we presented an aromatic1,3,4-oxadiazole-based chelation-enhanced fluorescence (CHEF) system as a highly selective fluorescent sensor for Zn2+in aqueous solution. It is expected that suitable metal ion could effectively electrophilic attack the hydroxyl oxygen atom with electron-rich property and torsional motions of the two aryl moieties in2-hydroxy-phenyl-1,3,4-oxadiazole group could be prevented, accompanied by the formation of rigid planar metal complex structure and simultaneous metal-induced block of nonradiative transitions to turn on the fluorescence signal. The fluorescence imaging of Zn2+in living cells was successfully applied by using fluorescence confocal microscopy, and the results revealed that the chemosensor can be utilized in living cells for monitoring Zn2+.
In the third section, two amide ligands with5-ary-1,3,4-oxadiazole were designed and synthesized. The fluorescence properties of their rare earth complexes were researched by modifying the different groups on the benzene ring to explore whether such conjugated skeleton structure could effectively sensitized rare earth ions. The results showed hydroxy group and twist of aromatic rings could affect the luminescence of rare earth complexes in solution.
In the last section, we designed and synthesized three5-aryl-1,3,4-oxadiazole-based organic compounds as organic solid-state light-emitting materials, which were characterized by NMR, X-ray and fluorescence spectra. The results showed that the molecule design could avoid concentration quenching of organic molecules and exhibit bright blue fluorescence in the solid state. The blue organic light-emitting semiconductor device of Pox-1was further prepared and measured.
第一章,简单介绍了荧光传感器和稀土配合物的研究背景和应用,重点介绍了Zn2+荧光传感器的配体分类和研究现状、稀土配合物的机理和设计
第二章,设计和合成了一种芳基-1,3,4-噁二唑类衍生物的荧光传感器。Zn2+离子通过亲电进攻,有效地与酚羟基上富含电子的氧原子结合,形成的金属配合物刚性平面结构可以阻止2-羟基-苯基-1,3,4-噁二唑中的二个芳香基团的扭转运动,抑制了金属诱导的无辐射跃迁,从而在水溶液中发出了亮蓝色荧光。我们成功地将该传感器L1应用于生物活细胞中,通过荧光共聚焦显微镜技术,实现了对肝癌细胞中高Zn2+离子浓度的荧光成像检测分析；
第三章,设计并合成了两种5-芳基-1,3,4-噁二唑类衍生物为骨架的酰胺型配体,考察该类配体骨架共轭结构能否有效敏化稀土配合物的特征荧光,并通过对苯环上官能团的取代,初步研究存在的羟基和芳香基团的扭转运动对稀土配合物固液状态下荧光的影响；
第四章,设计和合成了三个以5-芳基-1,3,4嗯二唑为主体的有机分子,并通过核磁和荧光光谱表征了这些化合物。荧光分析表明这些有机化合物在溶液中显示出弱的荧光,而在固态下表现出较强的亮蓝色荧光,从而避免了有机分子的浓度淬灭效应。我们将其中一个有机化合物蒸空镀膜制备成有机发光半导体器件,并对该器件进行了电致发光测试。
In this thesis, we have designed and synthesized some different5-aryl-1,3,4-oxadiazole-based ligands. The fluorescence response of L1to the metal ions, rare earth complexes of L2/L3and organic molecules devices prepared by Pox-1have also been investigated, respectively. The main contents including:
In the first section, we briefly describe the background and application of fluorescent chemosensors and the rare earth complexes. We especially focus on the classification of fluorescent sensors for zinc ion and design of rare earth complexes.
In the second section, we presented an aromatic1,3,4-oxadiazole-based chelation-enhanced fluorescence (CHEF) system as a highly selective fluorescent sensor for Zn2+in aqueous solution. It is expected that suitable metal ion could effectively electrophilic attack the hydroxyl oxygen atom with electron-rich property and torsional motions of the two aryl moieties in2-hydroxy-phenyl-1,3,4-oxadiazole group could be prevented, accompanied by the formation of rigid planar metal complex structure and simultaneous metal-induced block of nonradiative transitions to turn on the fluorescence signal. The fluorescence imaging of Zn2+in living cells was successfully applied by using fluorescence confocal microscopy, and the results revealed that the chemosensor can be utilized in living cells for monitoring Zn2+.
In the third section, two amide ligands with5-ary-1,3,4-oxadiazole were designed and synthesized. The fluorescence properties of their rare earth complexes were researched by modifying the different groups on the benzene ring to explore whether such conjugated skeleton structure could effectively sensitized rare earth ions. The results showed hydroxy group and twist of aromatic rings could affect the luminescence of rare earth complexes in solution.
In the last section, we designed and synthesized three5-aryl-1,3,4-oxadiazole-based organic compounds as organic solid-state light-emitting materials, which were characterized by NMR, X-ray and fluorescence spectra. The results showed that the molecule design could avoid concentration quenching of organic molecules and exhibit bright blue fluorescence in the solid state. The blue organic light-emitting semiconductor device of Pox-1was further prepared and measured.
引文
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