A new fluorescent chemosensor for F- based on inhibition of excited-state intramolecular proton transfer

被引：130
作者：
Jung, Hyci Sung [1 ]
Kim, Hyun Jung [1 ]
Vicens, Jacques [2 ]
Kim, Jong Seung [1 ]
机构：
[1] Korea Univ, Dept Chem, Seoul 136701, South Korea
[2] IPHC ULP ECPM CNRS, URA 7178, F-67087 Strasbourg, France
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 09期
基金：
新加坡国家研究基金会;
关键词：
Chemosensor; Anions; Anthraquinone; Calixarenes; ESIPT; ANION RECOGNITION; FLUORIDE; RECEPTORS; FUTURE;
D O I：
10.1016/j.tetlet.2008.12.026
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New fluorescent chemosensor 1 with two amidoanthraquinone groups (1-AAQs) at the lower rim of p-tert-butylcalix[4]arene has been synthesized. The significant changes of absorption and fluorescence bands show that chemosensor 1 is selective toward fluoride ion (F) over other anions such as Cl, Br, I, CH3COO, H2PO4, HSO4, and OH. The ESIPT process of 1 is inhibited by the fluoride-induced H-bonding followed by deprotonation of NH of the 1-AAQ. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：983 / 987
页数：5
相关论文
共 48 条
[1]   Supramolecular analytical chemistry [J].
Anslyn, Eric V. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :687-699
[2]   Synthesis and structural characterisation of the first bis(bora)calixarene:: a selective, bidentate, fluorescent fluoride sensor [J].
Arimori, S ;
Davidson, MG ;
Fyles, TM ;
Hibbert, TG ;
James, TD ;
Kociok-Köhn, GI .
CHEMICAL COMMUNICATIONS, 2004, (14) :1640-1641
[3]   EFFECT OF CYCLODEXTRIN COMPLEXATION ON THE PHOTOCHEMISTRY OF XANTHONE - ABSOLUTE MEASUREMENT OF THE KINETICS FOR TRIPLET-STATE EXIT [J].
BARRA, M ;
BOHNE, C ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8075-8079
[4]   Synthesis and ion sensing properties of new colorimetric and fluorimetric chemosensors based on bithienyl-imidazo-anthraquinone chromophores [J].
Batista, Rosa M. F. ;
Oliveira, Elisabete ;
Costa, Susana P. G. ;
Lodeiro, Carlos ;
Raposo, M. Manuela M. .
ORGANIC LETTERS, 2007, 9 (17) :3201-3204
[5]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO
[6]  
2-P
[7]   A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].
BENESI, HA ;
HILDEBRAND, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707
[8]   PHOTOINDUCED INTRAMOLECULAR PROTON-TRANSFER AS THE MECHANISM OF ULTRAVIOLET STABILIZERS - A REAPPRAISAL [J].
CATALAN, J ;
FABERO, F ;
GUIJARRO, MS ;
CLARAMUNT, RM ;
MARIA, MDS ;
FOCESFOCES, MD ;
CANO, FH ;
ELGUERO, J ;
SASTRE, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :747-759
[9]   A new class of functionalized calix[4]arenes as neutral receptors for colorimetric detection of fluoride ions [J].
Chawla, Har Mohindra ;
Shrivastava, Rahul ;
Sahu, Satya Narayan .
NEW JOURNAL OF CHEMISTRY, 2008, 32 (11) :1999-2005
[10]   A calix[4]imidazolium[2]pyridine as an anion receptor [J].
Chellappan, K ;
Singh, NJ ;
Hwang, IC ;
Lee, JW ;
Kim, KS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (19) :2899-2903
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