新型香豆素酰胺类化合物的合成及光学性能  

Syntheses and Optical Properties of Novel Amide-Containing Coumarin Derivatives

作　　者：贾建洪[1] 缪立威 李益珠 罗超群[1] 高建荣[1] 

机构地区：[1]浙江工业大学化学工程学院,浙江杭州310014

出　　处：《精细化工》2016年第7期736-740,824,共6页Fine Chemicals

基　　金：国家自然科学基金(21452001)~~

摘　　要：以水杨醛、氰基乙酸乙酯、3-氨基-4-羟基苯甲酸为原料,合成2-（2-羰基-2H-1-苯并吡喃-3-基）苯并口恶唑-5-羧酸,再经酰氯化和N-酰化反应合成8个新型香豆素酰胺类化合物,收率为41%~65%。用核磁共振谱、质谱和红外光谱对其结构进行了表征,并用UV-Vis和荧光光谱研究了其光学性能。结果表明：其π-π＊跃迁特征峰在250~255 nm;其最大吸收波长在345~360 nm;最大发射波长λem约为440 nm,Stokes位移约为90 nm,荧光量子产率约为0.05。其摩尔吸光系数达到了10^5L/（mol·cm）的数量级,是一类潜在的荧光材料。2-（ 2-Oxo-2H-1-benzopyran-3-yl） benzoxazole-5-carboxylic acid was synthesized from salicylaldehyde,ethyl cyanoacetate and 3-amino-4-hydroxybenzoic acid. Then,eight new amidecontaining coumarin derivatives with yields between 41% and 65% were synthesized via acylcholorination and N-acylation. Structures of the compounds were identified by nuclear magnetic resonance spectroscopy,mass spectroscopy and infrared spectroscopy. Their optical physical properties were investigated by UV- Vis and fluorescence spectroscopy. The results indicated that their absorption peak bands in the 250 to 255 nm region attributed to π-π＊transition,the maximum absorption wavelengths were between 345 and 360 nm,the emission maximum λemwas about 440 nm,the Stokes shift was about 90 nm and the fluorescence quantum yield was about 0. 05. Their molar absorption coefficients were about 10^5 L /（ mol · cm）. All data show that these amide-containing coumarin derivatives are a kind of potential fluorescent materials.

关 键 词：香豆素酰胺类 水杨醛 氰基乙酸乙酯 3-氨基-4-羟基苯甲酸 光学性能 功能材料 

分 类 号：O626[理学—有机化学]