Intramolecular Charge Transfer and Proton Transfer Fluorescence of Salicylanilides

Abstract

[中文文摘]将苯甲酰苯胺(BA)类电荷转移(CT)反应基团耦合到具有激发态分子内质子转移(ESIPT)反应通道的水杨酸(SA)分子中,设计合成了苯胺对/间位取代的水杨酰苯胺及其羟基甲基化衍生物邻甲氧基苯甲酰苯胺,考察了环己烷、乙醚、乙腈和甲醇中两类水杨酰苯胺衍生物吸收光谱和荧光光谱的溶剂效应和取代基效应.结果表明,水杨酰苯胺的荧光为SA-型质子转移(PT)荧光,对取代基的依赖性较小;当电子给体苯胺基的给电子能力提高时,如N-甲基水杨酰苯胺分子,其荧光为BA-型CT荧光.而羟基甲基化后的衍生物邻甲氧基苯甲酰苯胺则表现出与BA类似的荧光光谱特性,具有明显的取代基效应.认为水杨酰苯胺衍生物的激发态存在着相互竞争的BA-型CT和SA-型PT通道,二者可经苯胺基上取代基的电子效应调控.[英文文摘]The intramolecular charge transfer(CT)reaction known to occur in benzanilide(BA)derivatives was coupled to salicylic acid(SA)for understanding the substituent e ffect on the proton transfer fluorescence in comparison with that on the CT fluore scence.A series of salicylanilides1,in which the SA structural framewor k was incorporated in the electron acc eptor moiety of the BA-like CT fluoro phore,were designed and their absor ption and fluorescence spectra were investigated in aprotic solvents CHX,DEE,and ACN and protic solven MeOH.国家自然科学基金(20175020);福建省自然科学基金(D0220001);教育部优秀青年教师奖励计划(2001);德国大众基金(I/77072)资助项目

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