Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 345-351.DOI: 10.6023/cjoc202204054 Previous Articles     Next Articles



刘梦a, 黄延茹a, 孙小飞b,*(), 汤立军a,*()   

  1. a 渤海大学化学与材料工程学院 辽宁锦州 121013
    b 渤海大学食品科学与工程学院 辽宁锦州 121013
  • 收稿日期:2022-04-22 修回日期:2022-07-17 发布日期:2022-08-25
  • 通讯作者: 孙小飞, 汤立军
  • 基金资助:
    国家自然科学基金(21878023); 国家自然科学基金(U1608222); 辽宁特聘教授支持计划资助项目

An “Aggregation-Induced Emission+Excited-State Intramolecular Proton Transfer” Mechanisms-Based Benzothiazole Derived Fluorescent Probe and Its ClORecognition

Meng Liua, Yanru Huanga, Xiaofei Sunb(), Lijun Tanga()   

  1. a College of Chemistry and Materials Engineering, Bohai University, Jinzhou, Liaoning 121013
    b College of Food Science and Technology, Bohai University, Jinzhou, Liaoning 121013
  • Received:2022-04-22 Revised:2022-07-17 Published:2022-08-25
  • Contact: Xiaofei Sun, Lijun Tang
  • Supported by:
    National Natural Science Foundation of China(21878023); National Natural Science Foundation of China(U1608222); Program for Distinguished Professor of Liaoning Province

A fluorescent probe (Z)-O-(2-(benzo[d]thiazol-2-yl)-4-(2-cyano-2-(4-cyanophenyl)vinyl)-6-methylphenyl) dimeth- yl cabarmothioate (HBTY-N) based on benzothiazole derivatives was synthesized. The probe can recognize ClO with high selectivity through fluorescence Off-On change in Tris solution (pH=7). After adding ClO to the probe, the probe solution changed from no fluorescence to orange-red fluorescence, the Stokes shift is 235 nm, and the recognition response is fast. The detection limit of the probe HBTY-N for ClO is 2.127×10–7 mol/L, the applicable pH range is 1~10, and it has strong anti- interference ability. Mechanistic studies show that under the action of ClO, the probe releases the fluorophore (Z)-4-(2- (3-(benzo[d]thiazol-2-yl)-4-hydroxy-5-methylphenyl)-1-cyanovinyl)benzonitrile (HBTY) with “aggregation-induced emission (AIE)+excited-state intramolecular proton yransfer (ESIPT)” properties through the “oxidative deprotection” mechanism, and the quantum yield changes from 0 to 42.88%. In addition, the probe HBTY-N can perform fluorescence imaging of ClO in living cells with low cytotoxicity, and can also be used for the detection of ClO in actual water samples, which has potential application value.

Key words: aggregation-induced emission (AIE)+excited-state intramolecular proton yransfer (ESIPT), ClO, cell imaging, benzothiazole, fluorescent probe