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2020 , Vol. 40 >Issue 1: 186 - 193

DOI: https://doi.org/10.6023/cjoc201908019

研究简报

香豆素-咪唑类荧光染料的设计与研究

  • 后际挺 ,
  • 王冰雅 ,
  • 李坤 ,
  • 汪珊 ,
  • 余孝其
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  • a 信阳师范学院化学化工学院 河南信阳 464000;
    b 四川大学化学学院 成都 610064;
    c 湖北工程学院化学与材料科学学院 湖北孝感 432000

收稿日期: 2019-08-12

  修回日期: 2019-09-23

  网络出版日期: 2019-10-12

基金资助

国家自然科学基金（（Nos.21807029，21877082）、湖北省自然科学基金（No.2018CFB264）、信阳师范学院南湖学者奖励计划资助项目.

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Design and Study of Coumarin-Imidazol Dyes

  • Hou Jiting ,
  • Wang Bingya ,
  • Li Kun ,
  • Wang Shan ,
  • Yu Xiaoqi
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  • a College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang, He'nan 464000;
    b College of Chemistry, Sichuan University, Chengdu 610064;
    c School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, Hubei 432000

Received date: 2019-08-12

  Revised date: 2019-09-23

  Online published: 2019-10-12

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21807029, 21877082), the Hubei Provincial Natural Science Foundation (No. 2018CFB264) and the Nanhu Scholars Program for Young Scholars of XYNU (Xinyang Normal University).

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摘要

合成了不同给电子取代基（羟基、丁氧基、二乙基氨基等）的菲并[9，10-d]咪唑（CA1~CA6）或4，5-二苯基咪唑（CB1~CB6）修饰的香豆素衍生物，初步考察了它们的溶液发光和固体发光现象.研究表明，当香豆素取代基为氨基时，化合物在二氯甲烷中的荧光较强，而羟基取代、丁氧基取代或者无取代的衍生物在二氯甲烷中的荧光都很弱，而菲并[9，10-d]咪唑修饰的衍生物CA1~CA5的溶液荧光要比4，5-二苯基取代咪唑修饰的衍生物CB1~CB5的溶液强.另外，染料分子的分子内氢键强度及咪唑基-香豆素环间二面角大小都会对染料分子的发光性能产生影响.

关键词： 香豆素; 咪唑; 分子内氢键; 荧光

本文引用格式

后际挺 , 王冰雅 , 李坤 , 汪珊 , 余孝其 . 香豆素-咪唑类荧光染料的设计与研究[J]. 有机化学, 2020 , 40(1) : 186 -193 . DOI: 10.6023/cjoc201908019

Abstract

A series of phenanthro[9,10-d]imidazole (CA1~CA6) or 4,5-diphenyl imidazole (CB1~CB6) modified coumarin derivatives with different electron-donating substitutes were synthesized, and their fluorescences in organic solvent and solid were primarily explored. The results showed that the amino substituents in coumarin skelton enabled strong fluorescence in dichloromethane, while hydroxyl-, butoxyl-, or non-substituted derivatives showed very weak emission in dichloromethane. Meanwhile, phenanthro[9,10-d]imidazole modified coumarin dervatives CA1~CA5 exhibited stronger fluorescence than that of 4,5-diphenyl imidazole modified ones. Additionally, the strenghts of intramolecular hydrogen bond as well as the dihedral angles of the imidazole moiety and coumarin ring affected the optical properties of these dyes.

Key words： coumarin; imidazole; intramolecular hydrogen bond; fluorescence

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