The base-catalyzed reaction between thiol and epoxide functionalities is a simple process that can be carried out under ambient conditions. The base catalyst can be organic or inorganic. The reaction medium can be organic or aqueous. A variety of the required mercapto/oxirane-containing building blocks can be obtained from commercial sources. The reaction is highly efficient and regioselective. It is due to these attributes the thiol-epoxy reaction is referred to as a ‘click’ reaction. It produces a ß-hydroxy thioether linkage upon completion. The thioether group can be modified by a post-polymerization alkylation reaction to access antibiofouling and antibacterial ß-hydroxy sulfonium salts. Overall, therefore, the thiol-epoxy reaction is highly utilitarian in the context of polymer synthesis. Our aim in this article is to trace our own steps in this area of research and document the journey from initial simple synthetic efforts to the current functional materials prepared by the thiol-epoxy ‘click’ reaction.
|Number of pages
|Journal of Macromolecular Science, Part A: Pure and Applied Chemistry
|Published - 2022
Bibliographical noteFunding Information:
Financial support from the Ministry of Education Singapore under the AcRF Tier 1 (2019-T1-002-066) (RG106/19) (2018-T1-001-176) (RG18/18); Agency for Science, Technology and Research (A*STAR)-AME IRG A1883c0006; and NTU (04INS000171C230) is gratefully acknowledged. This research was also funded by National Research Foundation of Korea grant funded by the Korean government (MSIP) (NRF18R1D1A1B07048527).
© 2021 Taylor & Francis Group, LLC.
- click chemistry
- polysulfonium polyelectrolytes
- sulfur alkylation
- thiol-epoxy reaction
ASJC Scopus subject areas
- Ceramics and Composites
- General Chemistry
- Polymers and Plastics
- Materials Chemistry