Thiazole-based chemosensor III: synthesis and fluorescence sensing of CH3CO2- based on inhibition of ESIPT

被引:35
作者
Helal, Aasif [1 ]
Kim, Hong-Seok [1 ]
机构
[1] Kyungpook Natl Univ, Dept Appl Chem, Taegu 702701, South Korea
关键词
2-(2 '-Aminophenyl)thiazole; Urea; Fluorescence sensing; Acetate anion; ESIPT; INTRAMOLECULAR PROTON-TRANSFER; PYROPHOSPHATE SENSOR; ANION RECOGNITION; CHARGE-TRANSFER; ACETATE; RECEPTOR; WATER; FLUORIDE; 2-(2'-HYDROXYPHENYL)BENZIMIDAZOLE; CARBOXYLATES;
D O I
10.1016/j.tet.2010.07.007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel fluorogenic sensors based on urea derivative of 2-(2'-aminophenyl)-4-phenylthiazole (4 and 5) were prepared and used for recognition of anions with similar basicity and surface charge density. Chemosensor 4 was found to be highly selective to acetate ion over other anions. The selectivity was related to the structure matching between the host and the guest. The evaluation of the chemosensors' interaction with anions was performed by UV-vis and fluorescence titration. This acetate binding affinity was further tuned by varying the acidity of the N-H proton of the urea moiety in chemosensor 5. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7097 / 7103
页数:7
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