Water-Soluble Bis-triazolyl Benzochalcogendiazole Cycloadducts as Tunable Metal Ion Sensors

被引:37
作者
Bryant, Jonathan J. [1 ]
Lindner, Benjamin D. [1 ]
Bunz, Uwe H. F. [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
RECENT PROGRESS; FLUORESCENT; CRUCIFORMS; GOLD; CHEMOSENSORS; PROTONS; SILVER; HG2+;
D O I
10.1021/jo3024889
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of bis-triazolyl benzochalcogendiazoles was synthesized to investigate their metal-binding capabilities. These fluorophores were formed through the cycloaddition of an ethynylated benzochalcogendiazole and a water-soluble azide. Variation of the chalcogen heteroatom was seen to affect the photophysical properties as well as the metal-binding activity. These cycloadducts exhibited a distinct response to Cu2+, Ni2+, and Ag+ in water. The binding affinity for the copper and nickel ions increased moving the chalcogen atom from O to Se. Statistical analysis of the spectral data enabled differentiation of Ag+, Cu2+, and Ni2+ ions.
引用
收藏
页码:1038 / 1044
页数:7
相关论文
共 39 条
[1]  
[Anonymous], 2010, Chem. Soc. Rev, V39, P1221
[2]   Synthesis and characterization of a 2,1,3-benzothiadiazole-b-alkyne-b-1,4bis(2-ethylhexyloxy)benzene terpolymer, a stable low-band-gap poly(heteroaryleneethynylene) [J].
Bangcuyo, CG ;
Evans, U ;
Myrick, ML ;
Bunz, UHF .
MACROMOLECULES, 2001, 34 (22) :7592-7594
[3]   2,2′-Biimidazole-Based Conjugated Polymers as a Novel Fluorescent Sensing Platform for Pyrophosphate Anion [J].
Bao, Yinyin ;
Wang, Hu ;
Li, Qianbiao ;
Liu, Bin ;
Li, Qing ;
Bai, Wei ;
Jin, Bangkun ;
Bai, Ruke .
MACROMOLECULES, 2012, 45 (08) :3394-3401
[4]   Water-soluble benzo- and naphtho-thiadiazole-based bistriazoles and their metal-binding properties [J].
Brombosz, Scott M. ;
Appleton, Anthony Lucas ;
Zappas, Andrew J., II ;
Bunz, Uwe H. F. .
CHEMICAL COMMUNICATIONS, 2010, 46 (09) :1419-1421
[5]   Alkynylated Phenazines: Synthesis, Characterization, and Metal-Binding Properties of Their Bis-Triazolyl Cycloadducts [J].
Bryant, Jonathan J. ;
Zhang, Yexiang ;
Lindner, Benjamin D. ;
Davey, Evan A. ;
Appleton, Anthony Lucas ;
Qian, Xuhong ;
Bunz, U. H. F. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7479-7486
[6]   Photophysical property trends for a homologous series of bis-ethynyl-substituted benzochalcogendiazoles [J].
Coombs, Benjamin A. ;
Lindner, Benjamin D. ;
Edkins, Robert M. ;
Rominger, Frank ;
Beeby, Andrew ;
Bunz, Uwe H. F. .
NEW JOURNAL OF CHEMISTRY, 2012, 36 (03) :550-553
[7]   Cyclopenta[c]thiophene-Based D-A Conjugated Copolymers: Effect of Heteroatoms (S, Se, and N) of Benzazole Acceptors on the Properties of Polymers [J].
Das, Soumyajit ;
Pati, Palas Baran ;
Zade, Sanjio S. .
MACROMOLECULES, 2012, 45 (13) :5410-5417
[8]   New fluorescent chemosensors for metal ions in solution [J].
Formica, Mauro ;
Fusi, Vieri ;
Giorgi, Luca ;
Micheloni, Mauro .
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (1-2) :170-192
[9]   Atomistic Band Gap Engineering in Donor-Acceptor Polymers [J].
Gibson, Gregory L. ;
McCormick, Theresa M. ;
Seferos, Dwight S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :539-547
[10]   Recent progress on fluorescent chemosensors for metal ions [J].
Jeong, Yongsuk ;
Yoon, Juyoung .
INORGANICA CHIMICA ACTA, 2012, 381 :2-14