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
[1]   Crystal engineering of hydrogen-bonded assemblies -: A progress report [J].
Aakeröy, CB ;
Beatty, AM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (07) :409-+
[2]   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
[3]   Non-conventional hydrogen bonds [J].
Alkorta, I ;
Rozas, I ;
Elguero, J .
CHEMICAL SOCIETY REVIEWS, 1998, 27 (02) :163-170
[4]  
[Anonymous], 2011, CATFIGHT
[5]   Aluminium fluorescence detection with a FRET amplified chemosensor [J].
Arduini, M ;
Felluga, F ;
Mancin, F ;
Rossi, P ;
Tecilla, P ;
Tonellato, U ;
Valentinuzzib, N .
CHEMICAL COMMUNICATIONS, 2003, (13) :1606-1607
[6]   Definition of the hydrogen bond (IUPAC Recommendations 2011) [J].
Arunan, Elangannan ;
Desiraju, Gautam R. ;
Klein, Roger A. ;
Sadlej, Joanna ;
Scheiner, Steve ;
Alkorta, Ibon ;
Clary, David C. ;
Crabtree, Robert H. ;
Dannenberg, Joseph J. ;
Hobza, Pavel ;
Kjaergaard, Henrik G. ;
Legon, Anthony C. ;
Mennucci, Benedetta ;
Nesbitt, David J. .
PURE AND APPLIED CHEMISTRY, 2011, 83 (08) :1637-1641
[7]   Defining the hydrogen bond: An account (IUPAC Technical Report) [J].
Arunan, Elangannan ;
Desiraju, Gautam R. ;
Klein, Roger A. ;
Sadlej, Joanna ;
Scheiner, Steve ;
Alkorta, Ibon ;
Clary, David C. ;
Crabtree, Robert H. ;
Dannenberg, Joseph J. ;
Hobza, Pavel ;
Kjaergaard, Henrik G. ;
Legon, Anthony C. ;
Mennucci, Benedetta ;
Nesbitt, David J. .
PURE AND APPLIED CHEMISTRY, 2011, 83 (08) :1619-1636
[8]   Mapping Drug Architecture by MoStBioDat: Rapid Screening of Intramolecular Hydrogen Bonded Motifs in Catechols [J].
Bak, Andrzej ;
Magdziarz, Tomasz ;
Kurczyk, Agata ;
Polanski, Jaroslaw .
DRUG DEVELOPMENT RESEARCH, 2011, 72 (02) :209-218
[9]   A new fluorescent chemosensor for transition metal cations and on/off molecular switch controlled by pH [J].
Cao, YD ;
Zheng, QY ;
Chen, CF ;
Huang, ZT .
TETRAHEDRON LETTERS, 2003, 44 (25) :4751-4755
[10]   Hydrogen-Bonding Directed Assembly and Gelation of Donor-Acceptor Chromophores: Supramolecular Reorganization from a Charge-Transfer State to a Self-Sorted State [J].
Das, Anindita ;
Molla, Mijanur Rahaman ;
Banerjee, Ambar ;
Paul, Ankan ;
Ghosh, Suhrit .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) :6061-6066
123456