Click To Bind: Metal Sensors

被引:70
作者
Bryant, Jonathan J. [1 ]
Bunz, Uwe H. F. [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
click chemistry; copper; cycloaddition; sensors; triazoles; 1,3-DIPOLAR CYCLOADDITION; FLUORESCENT-PROBE; BUILDING-BLOCKS; TRIAZOLE; COORDINATION; CHEMOSENSOR; CHEMISTRY; AZIDE; LIGANDS; IONS;
D O I
10.1002/asia.201300260
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalyzed azide-alkyne click cycloaddition reaction is an efficient coupling reaction that results in the formation of a triazole ring. The wide range of applicable substrates for this reaction allows the construction of a variety of conjugated systems. The additional function of triazoles as metal-ion ligands has led to the click reaction being used for the construction of optical sensors for metal ions. The triazoles are integral binding elements, which are formed in an efficient modular synthesis. Herein, we review recent examples of triazoles as a metal-binding element in conjugated metal-ion sensors.
引用
收藏
页码:1354 / 1367
页数:14
相关论文
共 98 条
[1]  
[Anonymous], 2008, ANGEW CHEM INT ED, V47, P4926
[2]  
[Anonymous], 2008, ANGEW CHEM INT ED, V47, P3740
[3]  
[Anonymous], 2008, ANGEW CHEM INT EDIT, V47, P2649
[4]   Triazoles and tetrazoles: Prime ligands to generate remarkable coordination materials [J].
Aromi, Guillem ;
Barrios, Leoni A. ;
Roubeau, Olivier ;
Gamez, Patrick .
COORDINATION CHEMISTRY REVIEWS, 2011, 255 (5-6) :485-546
[5]   Reversing the Triazole Topology in a Cyclam-Triazole-Dye Ligand Gives a 10-Fold Brighter Signal Response to Zn2+ in Aqueous Solution [J].
Ast, Sandra ;
Rutledge, Peter J. ;
Todd, Matthew H. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (34) :5611-5615
[6]   1,3-dipolar cycloaddition for the generation of nanostructured semiconductors by heated probe tips [J].
Bakbak, Selma ;
Leech, Peter J. ;
Carson, Bradley E. ;
Saxena, Shubham ;
King, William P. ;
Bunz, Uwe H. F. .
MACROMOLECULES, 2006, 39 (20) :6793-6795
[7]   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
[8]   Water-Soluble Bis-triazolyl Benzochalcogendiazole Cycloadducts as Tunable Metal Ion Sensors [J].
Bryant, Jonathan J. ;
Lindner, Benjamin D. ;
Bunz, Uwe H. F. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03) :1038-1044
[9]   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
[10]   Poly(aryleneethynylene)s [J].
Bunz, Uwe H. F. .
MACROMOLECULAR RAPID COMMUNICATIONS, 2009, 30 (9-10) :772-805