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

被引：87
作者：
Duke, Rebecca M. [1 ]
Gunnlaugsson, Thorfinnur [1 ]
机构：
[1] Trinity Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 13期
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.
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收藏
页码：1503 / 1505
页数：3
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  • [11] Anion receptors based on organic frameworks:: highlights from 2005 and 2006
    Gale, Philip A.
    Garcia-Garrido, Sergio E.
    Garric, Joachim
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (01) : 151 - 190
  • [12] Preface: supramolecular chemistry of anionic species themed issue
    Gale, Philip A.
    Gunnlaugsson, Thorfinnur
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3595 - 3596
  • [13] Anion receptor chemistry: highlights from 2008 and 2009
    Gale, Philip A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3746 - 3771
  • [14] Colorimetric "naked eye" sensing of anions in aqueous solution
    Gunnlaugsson, T
    Kruger, PE
    Jensen, P
    Tierney, J
    Ali, HDP
    Hussey, GM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) : 10875 - 10878
  • [15] Dual responsive chemosensors for anions: the combination of fluorescent PET (photoinduced electron transfer) and colorimetric chemosensors in a single molecule
    Gunnlaugsson, T
    Kruger, PE
    Lee, TC
    Parkesh, R
    Pfeffer, FM
    Hussey, GM
    [J]. TETRAHEDRON LETTERS, 2003, 44 (35) : 6575 - 6578
  • [16] Simple naphthalimide based anion sensors:: deprotonation induced colour changes and CO2 fixation
    Gunnlaugsson, T
    Kruger, PE
    Jensen, P
    Pfeffer, FM
    Hussey, GM
    [J]. TETRAHEDRON LETTERS, 2003, 44 (49) : 8909 - 8913
  • [17] Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors
    Gunnlaugsson, Thorfinnur
    Glynn, Mark
    Tocci , Gillian M.
    Kruger, Paul E.
    Pfeffer, Frederick M.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2006, 250 (23-24) : 3094 - 3117
  • [18] Developing an anion host for lipid A binding and antibacterial activity
    Henderson, Luke C.
    Li, Jian
    Nation, Roger L.
    Velkov, Tony
    Pfeffer, Frederick M.
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (18) : 3197 - 3199
  • [19] Anion complexation and sensing using modified urea and thiourea-based receptors
    Li, Ai-Fang
    Wang, Jin-He
    Wang, Fang
    Jiang, Yun-Bao
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (10) : 3729 - 3745
  • [20] Fluoride ion-triggered dual fluorescence switch based on naphthalimides winged zinc porphyrin
    Li, Yang
    Cao, Lifeng
    Tian, He
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) : 8279 - 8282
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