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

页码：9600 / 9608

页数：9

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