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具有双光子荧光的新型香豆素类衍生物的合成及其光学性能
引用本文:方国顺,刘闯,薛震泳,冯燕. 具有双光子荧光的新型香豆素类衍生物的合成及其光学性能[J]. 合成化学, 2017, 25(11): 910-915. DOI: 10.15952/j.cnki.cjsc.1005-1511.2017.11.17061
作者姓名:方国顺  刘闯  薛震泳  冯燕
作者单位:安徽大学 化学化工学院,安徽 合肥 230601
基金项目:2015年安徽高校自然科学研究项目重点项目,2016年度安徽省自然科学基金
摘    要:以7-碘代香豆素-3-甲酸乙酯为原料通过Sonogashira偶联、酯水解和酰胺化反应合成了新型香豆素类衍生物--7-(4-甲氧基苯乙炔基)香豆素-3-N-炔丙基甲酰胺(4),其结构经1H NMR, 13C NMR, HR-MS(ESI)和元素分析表征。并对其紫外-可见吸收光谱、荧光发射光谱及双光子荧光光谱进行了研究。结果表明:溶剂极性对4的光学性质影响显著,4具有明显的溶致变色效应。此外,4具有较大的有效双光子吸收截面(在乙酸乙酯、甲苯和氯仿中分别为222.57、 168.98 和211.77 GM),并可发射较强的双光子诱导荧光。

关 键 词:7-碘代香豆素-3-甲酸乙酯  香豆素类衍生物  合成  溶致变色效应  双光子荧光  
收稿时间:2017-03-20

Synthesis and Optical Properties of A New Two-photon Fluorescent Coumarin Derivative
FANG Guo-shun,LIU Chuang,XUE Zhen-yong,FENG Yan. Synthesis and Optical Properties of A New Two-photon Fluorescent Coumarin Derivative[J]. Chinese Journal of Synthetic Chemistry, 2017, 25(11): 910-915. DOI: 10.15952/j.cnki.cjsc.1005-1511.2017.11.17061
Authors:FANG Guo-shun  LIU Chuang  XUE Zhen-yong  FENG Yan
Affiliation:School of Chemistry and Chemical Engineering, Anhui University, Hefei 230601, China
Abstract:A new coumarin derivative , 7-( 4-methoxyphenylethynyl ) coumarin-3-N-propargyl for-mamide(4), was synthesized by Sonogashira couple reaction , ester hydrolysis and amidation reaction using 7-iodide-coumarin-3-ethyl formate as the raw material . The structure was characterized by 1H NMR, 13C NMR, HR-MS(ESI) and elemental analysis.UV-Vis absorption spectra, single photon fluorescence spectra and two-photon fluorescence spectra were investigated .The results showed that the polarity of the solvent had a significant effect on the optical properties of 4, and 4 had the obvious sol-vatochromic effects.Moreover, 4 had the large two-photon excitation action cross sections (222.57 GM in ethyl acetate, 168.98 GM in toluene and 211.77 GM in chloroform) and can emit strong two-pho-ton-induced fluorescence .
Keywords:7-iodide-coumarin-3-ethyl formate  coumarin derivative  synthesis  solvatochromic effect  two-photon fluorescence
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