3-Urea-1,8-naphthalimides are good chemosensors: a highly selective dual colorimetric and fluorescent ICT based anion sensor for fluoride

被引:89
作者
Duke, Rebecca M. [1 ]
Gunnlaugsson, Thorfinnur [1 ]
机构
[1] Trinity Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
基金
爱尔兰科学基金会;
关键词
PHOTOINDUCED ELECTRON-TRANSFER; NAKED-EYE; RECOGNITION; BINDING; RECEPTORS; 4-AMINO-1,8-NAPHTHALIMIDE; DEPROTONATION; THIOUREA;
D O I
10.1016/j.tetlet.2011.01.099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,8-naphthalimide sensor 1 was developed as a colorimetric and fluorescent sensor for anions. Being the first example of such anion sensors, where the 3-position of the naphthalimide ring is used to incorporate the anion recognition moiety, in this case a trifluromethyl derived aryl urea moiety, the sensors gave rise to significant changes in both the absorption and the emission spectra, which were both red shifted upon interacting with anions. The changes were most pronounced for fluoride, and to a lesser extent for acetate and hydrogen phosphate, in DMSO, making 1 a highly selective sensor for F-. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1503 / 1505
页数:3
相关论文
共 39 条
[1]   Colorimetric 'naked-eye' and fluorescent sensors for anions based on amidourea functionalised 1,8-naphthalimide structures: anion recognition via either deprotonation or hydrogen bonding in DMSO [J].
Ali, Haslin Dato Paduka ;
Kruger, Paul E. ;
Gunnlaugsson, Thorfinnur .
NEW JOURNAL OF CHEMISTRY, 2008, 32 (07) :1153-1161
[2]   Anion recognition by hydrogen bonding: urea-based receptors [J].
Amendola, Valeria ;
Fabbrizzi, Luigi ;
Mosca, Lorenzo .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) :3889-3915
[3]   A simple colorimetric and fluorescent anion sensor based on 4-amino-1,8-naphthalimide: Synthesis and its recognition properties [J].
Bao, Xiao-Ping ;
Wang, Lei ;
Wu, Lei ;
Li, Zao-Ying .
SUPRAMOLECULAR CHEMISTRY, 2008, 20 (05) :467-472
[4]   Recognition and sensing of fluoride anion [J].
Cametti, Massimo ;
Rissanen, Kari .
CHEMICAL COMMUNICATIONS, 2009, (20) :2809-2829
[5]  
de Silva AP, 1996, NEW J CHEM, V20, P871
[6]   Selective fluorescent PET sensing of fluoride (F-)using naphthalimide-thiourea and -urea conjugates [J].
Duke, Rebecca M. ;
Gunnlaugsson, Thorfinnur .
TETRAHEDRON LETTERS, 2007, 48 (45) :8043-8047
[7]   Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors [J].
Duke, Rebecca M. ;
Veale, Emma B. ;
Pfeffer, Frederick M. ;
Kruger, Paul E. ;
Gunnlaugsson, Thorfinnur .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) :3936-3953
[8]   Luminescence anion sensing via modulation of MLCT emission from a naphthalimide-Ru(II)-polypyridyl complex [J].
Elmes, Robert B. P. ;
Gunnlaugsson, Thorfinnur .
TETRAHEDRON LETTERS, 2010, 51 (31) :4082-4087
[9]   Why, on interaction of urea-based receptors with fluoride, beautiful colors develop [J].
Esteban-Gómez, D ;
Fabbrizzi, L ;
Licchelli, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) :5717-5720
[10]   Boron based anion receptors as sensors [J].
Galbraith, Ewan ;
James, Tony D. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) :3831-3842