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

被引:1192
|
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 50 条
  • [1] Building Covalent Molecular Capsules by Thiol-Michael Addition Click Reaction
    Perretti, Marcelle D.
    Perez-Marquez, Lidia A.
    Garcia-Rodriguez, Raul
    Carrillo, Romen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02): : 840 - 850
  • [2] Thiol-Michael "click" chemistry: another efficient tool for head functionalization of giant surfactants
    Li, Yiwen
    Su, Hao
    Feng, Xueyan
    Wang, Zhao
    Guo, Kai
    Wesdemiotis, Chrys
    Fu, Qiang
    Cheng, Stephen Z. D.
    Zhang, Wen-Bin
    [J]. POLYMER CHEMISTRY, 2014, 5 (21) : 6151 - 6162
  • [3] High Generation Dendrimers via Thiol-Michael Click Chemistry
    Frayne, Stephen
    Northrop, Brian
    [J]. BIOPHYSICAL JOURNAL, 2014, 106 (02) : 419A - 419A
  • [4] Phototriggered base proliferation: a powerful 365 nm LED photoclick tool for nucleophile-initiated thiol-Michael addition reaction
    Xu, Ruixin
    Guan, Xiaoyuan
    He, Minghui
    Yang, Jianwen
    [J]. RSC ADVANCES, 2017, 7 (02): : 914 - 918
  • [5] Fabrication of micropatterned gold nanoparticles on graphene oxide nanosheet via thiol-Michael addition click chemistry
    Nie, Lei
    Zhang, Jingjing
    Wu, Qiaoyun
    Fei, Guanghai
    Hu, Kehui
    Fang, Liang
    Yang, Shoufeng
    [J]. MATERIALS LETTERS, 2020, 261
  • [6] Multifunctional Hair Dyeing with Curcumin via Thiol-Michael Click Reaction
    Wu, Yuwen
    Ma, Ling
    Li, Zhizhen
    Chen, Timson
    Chang, Kuan
    Komarneni, Sridhar
    Wang, Jing
    [J]. ACS APPLIED ENGINEERING MATERIALS, 2024, 2 (03): : 582 - 592
  • [7] A fluorinated branched polyether for PEO-based polymer electrolyte via thiol-Michael addition click reaction
    Tian, Jianling
    Li, Ruiyang
    Yang, Xueying
    Lai, Pengbin
    Liu, Jiaxiang
    Ye, Ruilai
    Deng, Yi
    Chen, Qichen
    Zhang, Peng
    Zhao, Jinbao
    [J]. SOLID STATE IONICS, 2024, 412
  • [8] Ionic liquid catalyzed thiol-Michael addition reaction in fluorescent probe
    Zuo, Yujing
    Gou, Zhiming
    Tian, Minggang
    Zhan, Jingting
    Lin, Weiying
    [J]. SENSORS AND ACTUATORS B-CHEMICAL, 2023, 393
  • [9] Rapid Hyperbranched Polythioether Synthesis Through Thiol-Michael Addition Reaction
    Daglar, Ozgun
    Gungor, Begum
    Guric, Gulce
    Gunay, Ufuk Saim
    Hizal, Gurkan
    Tunca, Umit
    Durmaz, Hakan
    [J]. JOURNAL OF POLYMER SCIENCE, 2020, 58 (06) : 824 - 830
  • [10] Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry
    Ho, The Hien
    Levere, Martin
    Soutif, Jean-Claude
    Montembault, Veronique
    Pascual, Sagrario
    Fontaine, Laurent
    [J]. POLYMER CHEMISTRY, 2011, 2 (06) : 1258 - 1260