Selective and colorimetric fluoride chemosensors containing phenol hydroxyl and 1,3,4-oxadiazole groups

被引:22
作者
Ma, Jiantao [1 ]
Li, Zhe [1 ]
Zong, Yanqing [1 ]
Men, Yi [1 ]
Xing, Guowen [1 ]
机构
[1] Beijing Normal Univ, Beijing Key Lab Energy Convers & Storage Mat, Coll Chem, Beijing 100875, Peoples R China
关键词
Sensor; F-; Oxadiazole; Hydrogen bond; Fluorescence; FLUORESCENT SENSORS; PROTON-TRANSFER; NAKED-EYE; COMPLEX; ANIONS; DEPROTONATION; MOIETIES; PROBE;
D O I
10.1016/j.tetlet.2012.12.128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel anion sensors, methyl 4-(5(5-chloro-2-hydroxypheny1)-1,3,4-oxadiazol-2-y1) benzoate (L1) and methyl 4-(5-(2-hydroxypheny1)-1,3,4-oxadiazol-2-y1) benzoate (12) were reported. Their spectro-scopic and colorimetric properties in CH2Cl2/CH3CN (1:2, v/v) solution for F- sensing were investigated by naked-eye, UV-vis, and fluorescence measurements. Both molecules with coplanar structure possess adjacent phenolic hydroxyl and 1,3,4-oxadiazole units, resulting in a sufficiently strong intramolecular hydrogen bond to hinder the association of most anions, but not F-, with phenolic hydroxyl hydrogen. They displayed the same color changes from colorless to yellow but different optical shifts upon addition of F-. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1348 / 1351
页数:4
相关论文
共 33 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]  
Bassin E. B., 2007, APPL GEOCHEM, V22, P1017
[3]   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
[4]   Recognition and sensing of fluoride anion [J].
Cametti, Massimo ;
Rissanen, Kari .
CHEMICAL COMMUNICATIONS, 2009, (20) :2809-2829
[5]   A polymeric colorimetric sensor with excited-state intramolecular proton transfer for anionic species [J].
Chu, Qinghui ;
Medvetz, Doug A. ;
Pang, Yi .
CHEMISTRY OF MATERIALS, 2007, 19 (26) :6421-6429
[6]   Fluorescent sensors for organophosphorus nerve agent mimics [J].
Dale, TJ ;
Rebek, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4500-4501
[7]   Anion receptor chemistry [J].
Gale, Philip A. .
CHEMICAL COMMUNICATIONS, 2011, 47 (01) :82-86
[8]   Fluoride Ion Sensing by an Anion-π Interaction [J].
Guha, Samit ;
Saha, Sourav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) :17674-17677
[9]   Simple bisthiocarbonohydrazones as sensitive, selective, colorimetric, and switch-on fluorescent chemosensors for fluoride anions [J].
Han, Feng ;
Bao, Yuhui ;
Yang, Zhigang ;
Fyles, Thomas M. ;
Zhao, Jianzhang ;
Peng, Xiaojun ;
Fan, Jiangli ;
Wu, Yunkou ;
Sun, Shiguo .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (10) :2880-2892
[10]   Efficient Fluorescence Resonance Energy Transfer-Based Ratiometric Fluorescent Cellular Imaging Probe for Zn2+ Using a Rhodamine Spirolactam as a Trigger [J].
Han, Zhi-Xiang ;
Zhang, Xiao-Bing ;
Zhuo Li ;
Gong, Yi-Jun ;
Wu, Xiang-Yang ;
Zhen Jin ;
He, Chun-Mei ;
Jian, Li-Xin ;
Jing Zhang ;
Shen, Guo-Li ;
Yu, Ru-Qin .
ANALYTICAL CHEMISTRY, 2010, 82 (08) :3108-3113