Azo dyes based on 8-hydroxyquinoline benzoates:: Synthesis and application as colorimetric Hg2+-selective chemosensors

被引:59
作者
Cheng, Yunfei
Zhang, Meng
Yang, Hong
Li, Fuyou [1 ]
Yi, Tao
Huang, Chunhui
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Fudan Univ, Adv Mat Lab, Shanghai 200433, Peoples R China
关键词
azo dyes; 8-hydroxyquinoline benzoates; colorimetric Hg2+-selective chemosensor;
D O I
10.1016/j.dyepig.2007.01.022
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of 8-hydroxyquinoline benzoates with diverse azo substituents were synthesized by diazo-reaction of 2-methyl-8-hydroxyquinoline with some arylamines, followed by esterification with benzoyl chloride. All the products allowed selective sensing with Hg2+, Which was affirmed by UV-vis absorption spectra. Different spectral changes were observed for these compounds with electron-donating substituent (bathochromic shift) or electron-withdrawing substituent (hypsochromic shift). Particularly, obvious color change was observed for 5-(4-dimethylaminophenylazo)-2-methylquinolin-8-yl benzoate in the presence of Hg2+, which made it possible for distinguishing Hg2+ from other metal ions by naked eye. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:775 / 783
页数:9
相关论文
共 72 条
[1]  
[Anonymous], 1987, BINDING CONSTANTS
[2]   A squaraine-based chemosensor for Hg2+ and Pb2+ [J].
Basheer, MC ;
Alex, S ;
Thomas, KG ;
Suresh, CH ;
Das, S .
TETRAHEDRON, 2006, 62 (04) :605-610
[3]   Ecological effects, transport, and fate of mercury: a general review [J].
Boening, DW .
CHEMOSPHERE, 2000, 40 (12) :1335-1351
[4]   Carrier-based ion-selective electrodes and bulk optodes. 2. Ionophores for potentiometric and optical sensors [J].
Buhlmann, P ;
Pretsch, E ;
Bakker, E .
CHEMICAL REVIEWS, 1998, 98 (04) :1593-1687
[5]   Highly selective chromogenic and redox or fluorescent sensors of Hg2+ in aqueous environment based on 1,4-disubstituted azines [J].
Caballero, A ;
Martínez, R ;
Lloveras, V ;
Ratera, I ;
Vidal-Gancedo, J ;
Wurst, K ;
Tárraga, A ;
Molina, P ;
Veciana, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15666-15667
[6]   Synthesis and cation binding properties of new arylazo-and heteroarylazotetrathiacalix[4]arenes [J].
Chakrabarti, A ;
Chawla, HM ;
Francis, T ;
Pant, N ;
Upreti, S .
TETRAHEDRON, 2006, 62 (06) :1150-1157
[7]   Azocalix[4]arene-based chromogenic anion probes [J].
Chen, CF ;
Chen, QY .
NEW JOURNAL OF CHEMISTRY, 2006, 30 (02) :143-147
[8]   Azo 8-hydroxyquinoline benzoate as selective chromogenic chemosensor for Hg2+ and Cu2+ [J].
Cheng, Yun-Fei ;
Zhao, Da-Tong ;
Zhang, Meng ;
Liu, Zhi-Qiang ;
Zhou, Yi-Feng ;
Shu, Tian-Min ;
Li, Fu-You ;
Yi, Tao ;
Huang, Chun-Hui .
TETRAHEDRON LETTERS, 2006, 47 (36) :6413-6416
[9]   A new Hg2+-selective chromoionophore based on calix[4]arenediazacrown ether [J].
Choi, MJ ;
Kim, MY ;
Chang, SK .
CHEMICAL COMMUNICATIONS, 2001, (17) :1664-1665
[10]   The toxicology of mercury - Current exposures and clinical manifestations [J].
Clarkson, TW ;
Magos, L ;
Myers, GJ .
NEW ENGLAND JOURNAL OF MEDICINE, 2003, 349 (18) :1731-1737