Oxidative cyclization of thiosemicarbazone: an optical and turn-on fluorescent chemodosimeter for Cu(II)

被引:60
作者
Basu, Arghya [1 ]
Das, Gopal [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, Assam, India
关键词
SOLID-PHASE SYNTHESIS; ALDEHYDE THIOSEMICARBAZONES; HG2+-SELECTIVE CHEMODOSIMETER; ENHANCED FLUORESCENCE; SELECTIVE FLUORESCENT; AQUEOUS-SOLUTION; HG(II) DETECTION; METAL-IONS; HG2+ IONS; CU-II;
D O I
10.1039/c0dt01549k
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A weakly fluorescent thiosemicabazone (L1H) was found to be a selective optical and "turn-on" fluorescent chemodosimeter for Cu2+ ion in aqueous medium. A significant fluorescence enhancement along with change in color was only observed for Cu2+ ion; among the other tested metal ions (viz. Na+, K+, Mg2+, Ca2+, Cr3+, Zn2+, Cd2+, Hg2+, Pb2+, Ag+, Ni2+, Co2+, Fe3+ and Mn2+). The Cu2+ selectivity resulted from an oxidative cyclization of the weak fluorescent L1H into highly fluorescent rigid 4,5-dihydro-5,5-dimethyl-4-(naphthalen-5-yl)-1,2,4-triazole-3-thione (L-2). The signaling mechanism has been confirmed by independent synthesis with detail characterization of L-2.
引用
收藏
页码:2837 / 2843
页数:7
相关论文
共 75 条
[1]   Thiomethoxychalcone-Functionalized Ferrocene Ligands as Selective Chemodosimeters for Mercury(II): Single-Crystal X-ray Structural Signature of the [Hg8(μ8-S)(SCH3)12]2+ Cluster [J].
Ahamed, B. Nisar ;
Arunachalam, M. ;
Ghosh, Pradyut .
INORGANIC CHEMISTRY, 2010, 49 (10) :4447-4457
[2]   Synthetic, structural and kinetic studies on the binding of cyclohexane-1,2-bis(4-methyl-3-thiosemicarbazone) to divalent metal ions (Co, Ni, Cu, Zn or Cd) [J].
Al-Karawi, Ahmed Jasim M. ;
Clegg, William ;
Harrington, Ross W. ;
Henderson, Richard A. .
DALTON TRANSACTIONS, 2009, (03) :564-570
[3]  
[Anonymous], 1995, SMART SAINT XPREP
[4]  
[Anonymous], 1999, SADABS:Software for Empirical Absorption Correction
[5]   Neurodegenerative diseases and oxidative stress [J].
Barnham, KJ ;
Masters, CL ;
Bush, AI .
NATURE REVIEWS DRUG DISCOVERY, 2004, 3 (03) :205-214
[6]   Synthesis and solution structure analysis of a bispyrenyl bishydroxamate calix[4]arene-based receptor, a fluorescent chemosensor for Cu2+and Ni2+ metal ions [J].
Bodenant, B ;
Weil, T ;
Businelli-Pourcel, M ;
Fages, F ;
Barbe, B ;
Pianet, I ;
Laguerre, M .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7034-7039
[7]  
BRICKS JL, 2000, J CHEM SOC P2, P1209
[8]   Biological inorganic and bioinorganic chemistry of neurodegeneration based on prion and Alzheimer diseases [J].
Brown, DR ;
Kozlowski, H .
DALTON TRANSACTIONS, 2004, (13) :1907-1917
[9]   Photocyclization reaction of some 2-methyl-4-phenyl- substituted aldehyde thiosemicarbazones. Mechanistic aspects [J].
Buscemi, S ;
Gruttadauria, M .
TETRAHEDRON, 2000, 56 (07) :999-1004
[10]   Main group metal complexes of semicarbazones and thiosemicarbazones.: A structural review [J].
Casas, JS ;
García-Tasende, MS ;
Sordo, J .
COORDINATION CHEMISTRY REVIEWS, 2000, 209 :197-261