几种杂环类偶氮化合物的合成与光致变色性能研究  

The synthesis and photochromism of several heterocyclic azo compounds

作　　者：朱少萍[1] 张秋云[1] 廉鹏程 乐传俊[1] Zhu Shaoping Zhang Qiuyun Lian Pengcheng Yue Chuanjun(School of Science and Chemical Engineering of Changzhou Institute of Technology, Changzhou 213002)

机构地区：[1]常州工学院数理与化工学院,常州213002

出　　处：《化工新型材料》2016年第10期103-105,共3页New Chemical Materials

基　　金：江苏省自然科学资金项目(BK2011235);江苏省教育厅指导性项目(08kjd30001)

摘　　要：合成了3-（2-（5-硝基噻唑）偶氮）-2-氨基-4-羟基吡啶、5-（2-（5-硝基噻唑）偶氮）-8-羟基喹啉、3-（2-（5-硝基噻唑）偶氮）-4-甲基-2-氨基吡啶、3-（2-（5-硝基噻唑）偶氮）-5-甲基-2-氨基吡啶、3-（2-（5-甲基噻唑）偶氮）-2-氨基吡啶、3-（2-（5-甲基噻唑）偶氮）-5-甲基-2-氨基吡啶（以下分别简称为化合物A,化合物B,化合物C,化合物D,化合物E,化合物F）,采用IR和1 H-NMR对其结构进行了表征,利用UV-Vis研究了其光致变色的性能。结果显示：化合物A,化合物B,化合物C,化合物D具有较为明显的光致变色的性能。在重氮环上引入吸电子基,而在偶合环上引入供电子基时,有利于共轭体系中电子流动,在520~550nm出现顺式吸收峰,表现出光致变色的性能。化合物E和化合物F的重氮环和偶合环上都引入供电子基,共轭体系中电子流动受阻,没有出现顺式吸收峰,因而不具有光致变色性,重氮环上的取代基的种类对光致变色性能具有重要的影响。Compounds 3-（2-（5-nitrothiazole） zao）-4-hydroxyl-2-aminopyridine, 5-（2-（5-nitrothiazole） zao）-8 hydrox-ylquinoline, 3-（ 2-（ 5-nitrothiazole ） zao ）-4-methyl-2-aminopyridine, 3- （ 2-（ 5-nitrothiazole ） zao ）-5-methyl-2-aminopyridine,3-（2-（5-methylthiazole） zao）-2-amino-pyridine, 3-（ 2-（5-methylthiazole） zao）-5-methyl-2-aminopyridine were synthesizedwhich were known simply as A,B,C,D,E,F. IR and 1 H-NMR were used to characterize compounds A-F. The photochro- mism of compounds were studied by UV-Vis spectra. The results showed that azo compounds A-D exhibited distinct pho- tochromism. When introducing the electron-withdrawing substituents on the diazo ring and the electron-donating substitu- ents on the azo ring which helped the electron flow in the conjugated system, the absorption bands of cis isomers were prone to occur at 520nm to 550nm and the compounds were more easily to show photochromism. The substituents on the diazo ring and the zao ring of compounds E and F were all electron donating,so the electron flow was hindered and no cis isomer absorption bands emerged and compounds E and F showed no photochromism. All the results illustrated that the species of the substituents had a vital effect on photochromism.

关 键 词：杂环偶氮化物 光致变色 取代基效应 反-顺光致异构化 

分 类 号：O626[理学—有机化学] TB34[理学—化学]