2-(1,2,3-Triazol-4-yl)pyridine-containing ethynylarenes as selective 'turn-on' fluorescent chemosensors for Ni(II)

被引:14
作者
Christensen, Joseph A. [1 ]
Fletcher, James T. [1 ]
机构
[1] Creighton Univ, Dept Chem, Omaha, NE 68178 USA
关键词
Sensor; Fluorescent; Ratiometric; Ni(II) detection; 1,2,3-Triazole; CONFORMATIONAL RESTRICTION; TERMINAL ALKYNES; SCHIFF-BASE; FLUOROPHORES; SENSOR; CYCLOADDITION; CYCLODEXTRIN; RECOGNITION; COMPLEXES; DISCOVERY;
D O I
10.1016/j.tetlet.2014.06.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of ethynylarene compounds containing 2-(1,2,3-triazol-4-yl)pyridine chelating units were studied as fluorescent chemosensors for metal cations in aqueous solution. Analogs possessing two chelating units bridged by either 1,4-diethynylphenyl or 2,7-diethynylnaphthyl subunits displayed large hypsochromic shifts coupled with signal intensification when exposed to increasing concentrations of Ni(II), a unique response among 22 metal cation analytes. This response was shown to be reversible, and is proposed to derive from disruption of aggregate formation upon Ni(II) binding at the peripheral chelating units. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4612 / 4615
页数:4
相关论文
共 42 条
[11]   Exploiting the versatile assembly of arylpyridine fluorophores for wavelength tuning and SAR [J].
Fang, AG ;
Mello, JV ;
Finney, NS .
ORGANIC LETTERS, 2003, 5 (07) :967-970
[12]   Combinatorial discovery of fluorophores and fluorescent probes [J].
Finney, NS .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2006, 10 (03) :238-245
[13]   Monosubstituted 1,2,3-triazoles from two-step one-pot deprotection/click additions of trimethylsilylacetylene [J].
Fletcher, James T. ;
Walz, Sara E. ;
Keeney, Matthew E. .
TETRAHEDRON LETTERS, 2008, 49 (49) :7030-7032
[14]   Multidentate 1,2,3-Triazole-Containing Chelators from Tandem Deprotection/Click Reactions of (Trimethylsilyl)alkynes and Comparison of Their Ruthenium(II) Complexes [J].
Fletcher, James T. ;
Bumgarner, Benjamin J. ;
Engels, Nicole D. ;
Skoglund, David A. .
ORGANOMETALLICS, 2008, 27 (21) :5430-5433
[15]   Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II), and Zn(II) [J].
Fletcher, James T. ;
Bruck, Brent S. ;
Deever, Douglas E. .
TETRAHEDRON LETTERS, 2013, 54 (39) :5366-5369
[16]   1-Allyl- and 1-Benzyl-3-methyl-1,2,3-triazolium Salts via Tandem Click Transformations [J].
Fletcher, James T. ;
Keeney, Matthew E. ;
Walz, Sara E. .
SYNTHESIS-STUTTGART, 2010, (19) :3339-3345
[17]   Green fluorescence poly(amidoamine) dendrimer functionalized with 1,8-naphthalimide units as potential sensor for metal cations [J].
Grabchev, Ivo ;
Chovelon, Jean-Marc ;
Nedelcheva, Ana .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2006, 183 (1-2) :9-14
[18]   One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides [J].
Ladouceur, Sebastien ;
Soliman, Ahmed M. ;
Zysman-Colman, Eli .
SYNTHESIS-STUTTGART, 2011, (22) :3604-3611
[19]   Construction of a Novel Zn-Ni Trinuclear Schiff Base and a Ni2+ Chemosensor [J].
Li, Guo-Bi ;
Fang, Hua-Cai ;
Cai, Yue-Peng ;
Zhou, Zheng-Yuan ;
Thallapally, Praveen K. ;
Tian, Jian .
INORGANIC CHEMISTRY, 2010, 49 (16) :7241-7243
[20]   Novel coumarin fluorescent dyes: Synthesis, structural characterization and recognition behavior towards Cu(II) and Ni(II) [J].
Li, Hongqi ;
Cai, Li ;
Li, Jinxing ;
Hu, Yixin ;
Zhou, Pingping ;
Zhang, Jiming .
DYES AND PIGMENTS, 2011, 91 (03) :309-316