摘要
合成了一种基于苯并噻唑衍生物的荧光探针(Z)-O-(2-(苯并[d]噻唑-2-基)-4-(2-氰基-2-(4-氰基苯基)乙烯基)-6-甲基苯基)二甲基硫代氨基甲酸酯(HBTY-N),探针在Tris溶液(p H=7)中能够通过荧光“Off-On”变化,高选择性识别Cl O^(-).向该探针中加入ClO-后溶液由无荧光变为橙红色荧光,斯托克位移为235nm,且识别响应快速.探针HBTY-N对ClO-的检测限为2.127×10^(-7 )mol/L, pH适用范围为1~10,并且有较强的抗干扰能力.机理研究表明,在ClO-的作用下,探针通过“氧化去保护”机制释放出具有“聚集诱导发光+激发态分子内质子转移(AIE+ESIPT)”性质的荧光团(Z)-4-(2-(3-(苯并[d]噻唑-2-基)-4-羟基-5-甲基苯基)-1-氰基乙烯基)苄腈(HBTY),量子产率由0变为42.88%.此外,探针HBTY-N可对活细胞中ClO-进行荧光成像,且对细胞毒性低,还可用于实际水样中的ClO^(-)检测,具有潜在的应用价值.
A fluorescent probe(Z)-O-(2-(benzo[d]thiazol-2-yl)-4-(2-cyano-2-(4-cyanophenyl)vinyl)-6-methylphenyl) dimethyl 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 antiinterference 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.
作者
刘梦
黄延茹
孙小飞
汤立军
Liu Meng;Huang Yanru;Sun Xiaofei;Tang Lijun(College of Chemistry and Materials Engineering,Bohai University,Jinzhou,Liaoning 121013;College of Food Science and Technology,Bohai University,Jinzhou,Liaoning 121013)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2023年第1期345-351,共7页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(Nos.21878023,U1608222)
辽宁特聘教授支持计划资助项目。
