The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry

被引:1284
作者
Nair, Devatha P. [1 ]
Podgorski, Maciej [1 ,2 ]
Chatani, Shunsuke [1 ]
Gong, Tao [1 ]
Xi, Weixian [3 ]
Fenoli, Christopher R. [3 ]
Bowman, Christopher N. [1 ,3 ,4 ]
机构
[1] Univ Colorado, Dept Chem & Biol Engn, Boulder, CO 80303 USA
[2] MCS Univ, Dept Polymer Chem, Fac Chem, PL-20031 Lublin, Poland
[3] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA
[4] Univ Colorado, Mat Sci & Engn Program, Boulder, CO 80309 USA
关键词
thiol-Michael addition reaction; thiol-click chemistry; thiol-Michael addition reaction mechanism; CATALYTIC CHAIN TRANSFER; ELECTRON-WITHDRAWING GROUPS; CONJUGATE ADDITION; ENE CLICK; SURFACE MODIFICATION; GLYCOL) HYDROGELS; VINYL SULFONES; ACRYLATE PHOTOPOLYMERS; THERMAL REVERSIBILITY; DEGRADATION BEHAVIOR;
D O I
10.1021/cm402180t
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The key attribute of the thiol-Michael addition reaction that makes it a prized tool in materials science is its modular "click" nature, which allows for the implementation of this highly efficient, "green" reaction in applications that vary from small molecule synthesis to in situ polymer modifications in biological systems to the surface functionalization of material coatings. Over the past few decades, interest in the thiol-Michael addition reaction has increased dramatically, as is evidenced by the number of studies that have been dedicated to elucidating different aspects of the reaction that range from an in-depth analysis aimed at understanding the mechanistic pathways of the reaction to synthetic studies that have examined modifying molecular structures with the aim of yielding highly efficient thiol-Michael reaction monomers. This review examines the reaction mechanisms, the substrates and catalysts used in the reaction, and the subsequent implementation of the thiol-Michael reaction in materials science over the years, with particular emphasis on the recent developments in the arena over the past decade.
引用
收藏
页码:724 / 744
页数:21
相关论文
共 142 条
[71]   Thiol-Isocyanate-Acrylate Ternary Networks by Selective Thiol-Click Chemistry [J].
Matsushima, Hironori ;
Shin, Junghwan ;
Bowman, Christopher N. ;
Hoyle, Charles E. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2010, 48 (15) :3255-3264
[72]  
McDaid P, 2002, ANGEW CHEM INT EDIT, V41, P338, DOI 10.1002/1521-3773(20020118)41:2<338::AID-ANIE338>3.0.CO
[73]  
2-M
[74]   Dual-functional materials via CCTP and selective orthogonal thiol-Michael addition/epoxide ring opening reactions [J].
McEwan, Kayleigh A. ;
Slavin, Stacy ;
Tunnah, Edward ;
Haddleton, David M. .
POLYMER CHEMISTRY, 2013, 4 (08) :2608-2614
[75]   Network formation and degradation behavior of hydrogels formed by Michael-type addition reactions [J].
Metters, A ;
Hubbell, J .
BIOMACROMOLECULES, 2005, 6 (01) :290-301
[76]  
Michael A., 1887, AM CHEM J, V9, P115
[77]   KF/Al2O3-Mediated Michael addition of thiols to electron-deficient olefins [J].
Moghaddam, FM ;
Bardajee, GR ;
Veranlou, ROC .
SYNTHETIC COMMUNICATIONS, 2005, 35 (18) :2427-2433
[78]  
Movassagh B., 2012, Int. J. Org. Chem, V2, P248, DOI [10.4236/ijoc.2012.23033, DOI 10.4236/IJOC.2012.23033]
[79]   Nanocubes and nanoboxes [J].
Murphy, CJ .
SCIENCE, 2002, 298 (5601) :2139-+
[80]   Two-Stage Reactive Polymer Network Forming Systems [J].
Nair, Devatha P. ;
Cramer, Neil B. ;
Gaipa, John C. ;
McBride, Matthew K. ;
Matherly, Emily M. ;
McLeod, Robert R. ;
Shandas, Robin ;
Bowman, Christopher N. .
ADVANCED FUNCTIONAL MATERIALS, 2012, 22 (07) :1502-1510