Hydrogen bond induced fluorescence recovery of coumarin-based sensor system

被引：21
作者：
Huang, Xiaobo [1 ,2 ]
Dong, Yu [2 ]
Huang, Qianwen [1 ]
Cheng, Yixiang [2 ]
机构：
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Nanjing Univ, Sch Chem & Chem Engn, Key Lab Mesoscop Chem MOE, Nanjing 210093, Jiangsu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 29期
基金：
中国国家自然科学基金;
关键词：
Hydrogen bond; Fluorescence chemosensor; Coumarin; pH detection; NAKED-EYE; PH; RECOGNITION; MOLECULES; STACKING; POLYMER; GUANINE; PROBE; ZINC; ION;
D O I：
10.1016/j.tetlet.2013.05.034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two coumarin-type fluorescent sensors were synthesized and their fluorescence response to pH value was investigated. The fluorescence intensity of sensor 3 and sensor 4 is obviously enhanced along with the increase of pH from 7 to 12 and the reduction of pH value from 8 to 1, respectively. Possible mechanism for these fluorescence recovery systems is proposed. Intramolecular hydrogen bond could be formed under different condition, which blocks electron transferring route from nitrogen atom to fluorophore. The blue fluorescence color change of the two sensory systems could be directly detected by naked eyes under UV-lamp for pH values. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码：3822 / 3825
页数：4
相关论文
共 55 条
[31]   Fluorogenic and chromogenic chemosensors and reagents for anions [J].
Martínez-Máñez, R ;
Sancenón, F .
CHEMICAL REVIEWS, 2003, 103 (11) :4419-4476
[32]   The ionic hydrogen bond [J].
Meot-Ner, M .
CHEMICAL REVIEWS, 2005, 105 (01) :213-284
[33]  
Pauling L., 1967, CHEM BOND BRIEF INTR
[34]   Metals in neurobiology: Probing their chemistry and biology with molecular imaging [J].
Que, Emily L. ;
Domaille, Dylan W. ;
Chang, Christopher J. .
CHEMICAL REVIEWS, 2008, 108 (05) :1517-1549
[35]   A coumarin-derived fluorescence probe selective for magnesium [J].
Ray, Debdas ;
Bharadwaj, P. K. .
INORGANIC CHEMISTRY, 2008, 47 (07) :2252-2254
[36]   HYDROGEN-BONDING, HYDROPHOBICITY, PACKING, AND PROTEIN-FOLDING [J].
ROSE, GD ;
WOLFENDEN, R .
ANNUAL REVIEW OF BIOPHYSICS AND BIOMOLECULAR STRUCTURE, 1993, 22 :381-415
[37]   Fluorescence sensor applications as detectors for DNA damage, free radical formation, and in microlithography [J].
Scaiano, JC ;
Aliaga, C ;
Chrétien, MN ;
Frenette, M ;
Focsaneanu, KS ;
Mikelsons, L .
PURE AND APPLIED CHEMISTRY, 2005, 77 (06) :1009-1018
[38]   Hydrogen bonding and stacking of DNA bases: A review of quantum-chemical ab initio studies [J].
Sponer, J ;
Leszczynski, J ;
Hobza, P .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1996, 14 (01) :117-135
[39]  
Steiner T, 2002, ANGEW CHEM INT EDIT, V41, P48, DOI 10.1002/1521-3773(20020104)41:1<48::AID-ANIE48>3.0.CO
[40]  
2-U
123456