新型香豆素酰胺类化合物的合成及光学性能

Syntheses and Optical Properties of the Novel Amide-Containing Coumarin Derivatives

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）苯并噁唑-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105 M-1•cm-1的数量级，是一类潜在的荧光材料。

Abstract:

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 amide-containing coumarin derivatives were synthesized via acylcholorination and N-acylation for the first time. The yields were between 41 % and 65 %. Their structures were identified by nuclear magnetic resonance spectroscopy, mass spectroscopy and infrared spectroscopy and treated with UV-Vis and fluorescence spectroscopy to investigate their optical physical properties. The results: the π-π* transition peaks were between 250 nm and 255 nm, the maximum absorption wavelengths were between 345 nm and 360 nm, the emission maximum λem was 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 105 M-1•cm-1, showed that they are a kind of potential fluorescent materials.