羟基-炔点击反应制备具有红移发射的非传统荧光化合物及性能  

Preparation and properties of unconventional fluorescent compounds with red-shifted emission by hydroxyl-yne click reaction

作　　者：张红燕 蒋其民 史凌月 张彤 蒋必彪 Zhang Hongyan;Jiang Qimin;Shi Lingyue;Zhang Tong;Jiang Bibiao(Jiangsu Key Laboratory of Environmentally Friendly Polymeric Materials,School of Materials Science and Engineering,Changzhou University,Changzhou 213164)

机构地区：[1]江苏省环境友好高分子材料重点实验室,常州大学材料科学与工程学院,常州213164

出　　处：《化工新型材料》2024年第1期238-242,共5页New Chemical Materials

基　　金：国家自然科学青年基金项目(51903020);江苏省自然科学青年基金项目(BK20190932)。

摘　　要：以丙炔酸甲酯为原料,分别与2-二乙基氨基乙醇、N-甲基二乙醇胺和三乙醇胺经常温羟基-炔点击反应在无催化剂和无溶剂条件下制备得到三组含叔胺和乙烯基醚非传统发色团的有机荧光化合物。利用傅里叶红外光谱仪(FT-IR)和核磁共振波谱仪(NMR)确证所得化合物的分子结构。利用紫外-可见分光光度计(UV-Vis)和荧光分光光度计探究了化合物的荧光性能,结果表明:所得三组化合物均表现出浓度增强发光及激发波长依赖荧光特性。以三乙醇胺、N-甲基二乙醇胺和2-二乙氨基乙醇分别反应所得化合物的发射波长依次红移,且其红移程度依赖于化合物的浓度,表现出结构和浓度依赖红移荧光特性。该方法实现了简单调控化合物的结构和浓度得到长波长的非传统有机荧光化合物,这为设计长波长非传统荧光材料提供了新的方法和思路。Three organic fluorescent compounds containing tertiary amines and vinyl ether unconventional chromophores were prepared under catalyst-free and solvent-free conditions by hydroxy-alkyne click reaction of methyl propiolate with 2-diethylaminoethanol,N-methyldiethanolamine and triethanolamine at room temperature,respectively.The structures of the obtained compounds were characterized by Fourier transform infrared spectroscopy(FT-IR) and nuclear magnetic resonance spectroscopy(NMR).The fluorescence properties of the compounds were investigated by ultraviolet-visible spectrophotometer(UV-Vis) and fluorescence spectrophotometer.It was found that the obtained compounds exhibited concentration-enhanced luminescence and excitation-dependent fluorescence properties.The emission wavelengths of the compounds obtained by triethanolamine,N-methyldiethanolamine and 2-diethylaminoethanol were red-shifted in order and the degree of red-shift depended on the concentration,showing the structure-and concentration-dependent red-shifted fluorescence properties.Thus,the unconventional organic fluorescent compounds with long emission wavelength could be obtained by simply regulating the structure and concentration,which provided a new and facile approach and idea for the design of long-wavelength unconventional fluorescent materials.

关 键 词：点击反应 有机荧光化合物 非传统发色团 红移 结构 

分 类 号：O623.7[理学—有机化学]