1D-π-A型偶氮苯衍生物合成、表征及其光致变色性能  

Synthesis,characterization and photochromic properties of D-π-A azobenzene derivatives

作　　者：宋秀美 冯宗财 汪朝阳[2] 曾慧娟 刘丽燕 詹超敏 

机构地区：[1]岭南师范学院产业技术研究院广东高校新材料工程技术开发中心,广东湛江524048 [2]华南师范大学化学与环境学院,广州510006

出　　处：《功能材料》2015年第9期9114-9119,共6页Journal of Functional Materials

基　　金：广东省自然科学基金资助项目(S2011010001544);广东省高等学校高层次人才(粤财教[2011]431号)和高分子材料工程国家重点实验室(四川大学)开放课题基金资助项目(KF201208)

摘　　要：以4-氨基硝基苯为起始原料,通过溴代、重氮去氨基、硝基还原制备出重要中间体3,5-二溴苯胺,再以3,5-二溴苯胺和3-溴苯胺分别与苯酚衍生物进行重氮偶合反应,合成了10个D-π-A 型偶氮苯衍生物,利用FTGIR、NMR、ESIGMS、元素分析和XG单晶衍射等表征方法,确定目标化合物结构,并通过UV-Vis光谱研究了系列目标化合物光致变色性能,测定其光致顺反异构速率常数.研究结果表明,目标化合物表现出显著光致变色性能,顺反异构转变速率常数数量级为10^-2-10^-3s^-1,异构转变速率快慢主要取决于化合物分子的取代基空间位阻大小.Starting from 4-nitroaniline,the key intermediate 3,5-dibromoaniline was obtained by sequential reactions of bromination,diazotization deamination and nitro-reduction.Then 3,5-dibromoaniline and 3-bromoaniline were reacted with phenol derivatives to give 10 novel D-π-A azobenzene derivatives via azo coupling respectively.The structures of the target compounds were confirmed by NMR,ESI-MS,elemental analysis and X-ray single crystal diffraction.The photochromic property was characterized by UV-Vis spectroscopy,and the reversible cis-trans isomerization speed constants were tested.The results indicate that the target compounds displayed sensitive photochromic response.The isomerization speeds constants ranged from 10-2 to 10-3 s-1.The isomerization speeds mainly depended on molecular steric hindrance.

关 键 词：D-π-A型偶氮苯 重氮偶合 光致变色 顺反异构 速率常数 

分 类 号：O625.6[理学—有机化学]