New regioisomeric naphthol thiazole based 'turn-on' fluorescent chemosensor for Al3+

被引：36
|
作者：
Helal, Aasif [1 ]
Kim, Hyun Gon [1 ]
Ghosh, Manik Kumer [2 ]
Choi, Cheol-Ho [2 ]
Kim, Sung-Hong [3 ]
Kim, Hong-Seok [1 ]
机构：
[1] Kyungpook Natl Univ, Dept Appl Chem, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Dept Chem, Taegu 702701, South Korea
[3] Korea Basic Sci Inst, Daegu Ctr, Anal Res Div, Taegu 702701, South Korea
来源：
TETRAHEDRON | 2013年 / 69卷 / 46期
基金：
新加坡国家研究基金会;
关键词：
Al3+-selective; Fluorescent chemosensor; Regioisomeric naphthol-thiazole; Turn-on; Al3+-promoted hydrolysis; INTRAMOLECULAR PROTON-TRANSFER; SELF-ORGANIZED ENSEMBLE; SELECTIVE CHEMOSENSOR; ALUMINUM TOXICITY; DERIVATIVES; SENSOR; WORKERS; WATER; MECHANISMS; EMISSION;
D O I：
10.1016/j.tet.2013.09.038
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new reactive and highly selective turn-on fluorescent chemosensors based on the position of ring annulation of the naphthalene thiazole moiety for aluminum ions in ethanol, were synthesized and investigated. It was found that sensors 2 and 4 exhibited a remarkable enhancement of emission upon complexation with Al3+. A TD-B3LYP/6-31G(d,p) calculation was performed to characterize the nature of the fluorescence behavior of sensors 2 and 4 upon Al3+ complexation. The mechanism of fluorescence was based on the cation promoted hydrolysis of ester and subsequent complexation. The combination of experimental and computational analyses provides a more complete understanding of the molecular level origin of these types of unique photophysical properties. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9600 / 9608
页数：9
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