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新型香豆素硼氟荧光染料的合成及其光学性能
引用本文:刘瑶,但飞君,鲁茜,张吉,兰海闯.新型香豆素硼氟荧光染料的合成及其光学性能[J].合成化学,2017,25(11):904-909.
作者姓名:刘瑶  但飞君  鲁茜  张吉  兰海闯
作者单位:三峡大学 生物与制药学院,湖北 宜昌 443002
基金项目:国家自然科学基金资助项目,三峡大学研究生科研创新基金,三峡大学高层次人才科研启动基金资助项目
摘    要:以邻氨基苯甲酸甲酯和4-二乙胺基水杨醛为原料,合成了一个新的香豆素喹啉衍生物3-{2-[8-(1H-苯并咪唑-2-基)喹啉-2-基]乙烯基}-7-二乙胺基香豆素(QMC),再与BF3·Et2O配位合成了硼氟配合物(BQMC),其结构经1H NMR和MS(ESI)表征。并对BQMC的光学性能进行了研究。结果表明:BQMC的最大吸收波长在二氧六环中为490 nm,在DMSO中为532 nm; BQMC的最大发射波长在正己烷中为618 nm,在DMSO中为679 nm,与配体QMC相比,最大吸收波长红移了近50 nm,最大发射波长红移了近100 nm, BQMC的Stokes位移值从115 nm增至183 nm。在固态下,BQMC在750~825 nm之间有较宽的荧光发射峰,具有较强荧光。

关 键 词:邻氨基苯甲酸甲酯  4-二乙胺基水杨醛  三氟化硼  苯并咪唑  喹啉  香豆素  合成  荧光光谱  紫外-可见光谱  
收稿时间:2017-04-15

Synthesis and Optical Properties of A Novel Coumarin Boron Difluoride Complex
LIU Yao,DAN Fei-jun,LU Xi,ZHANG Ji,LAN Hai-chuang.Synthesis and Optical Properties of A Novel Coumarin Boron Difluoride Complex[J].Chinese Journal of Synthetic Chemistry,2017,25(11):904-909.
Authors:LIU Yao  DAN Fei-jun  LU Xi  ZHANG Ji  LAN Hai-chuang
Affiliation:College of Biological and Pharmaceutical Science, China Three Gorges University, Yichang 443002, China
Abstract:3-{2-8-(1H-benzimidazol-2-yl) quinolin-2-yl] ethenyl}-7-diethylaminocoumarin ( QMC) was synthesized by the reaction of methyl anthranilate with 4-diethylamino salicylaldehyde .A novel coumarin boron difluoride complex(BQMC) was obtained by coordination of QMC with BF3· Et2O. The structure was characterized by 1H NMR and MS ( ESI ) .The optical properties of BQMC were in-vestigated .The results indicated that the maximum absorption wavelength of BQMC were 490 nm in dioxane and 532 nm in DMSO.The maximum emission wavelength of BQMC were 618 nm in n-hex-ane and 679 nm in DMSO.Compared with the ligand QMC, BQMC showed a nearly 50 nm red shift of the maximum absorption wavelength and a nearly 100 nm red shift of the maximum emission wave-length.And the Stokes shift of BQMC increased from 115 nm to 183 nm.In the solid membrane, BQMC had a wide fluorescence emission peak between 750 nm and 825 nm and exhibited strong fluo-rescence .
Keywords:methyl anthranilate  4-diethylamino salicylaldehyde  boron trifluoride  benzimidazole  quinolone  coumarin  synthesis  ultraviolet spectrum  fluorescence spectrum
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