Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts
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 blo...
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sg-ntu-dr.10356-1723472023-12-11T15:35:10Z Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts Stuparu, Mihaiela Corina Khan, Anzar School of Physical and Mathematical Sciences Science::Chemistry Polythioethers Polysulfonium Polyelectrolytes 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. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) Nanyang Technological University Submitted/Accepted version 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). 2023-12-06T07:14:07Z 2023-12-06T07:14:07Z 2022 Journal Article Stuparu, M. C. & Khan, A. (2022). Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 59(1), 2-10. https://dx.doi.org/10.1080/10601325.2021.1984849 1060-1325 https://hdl.handle.net/10356/172347 10.1080/10601325.2021.1984849 2-s2.0-85116567153 1 59 2 10 en 2019-T1-002-066 RG106/19 2018-T1-001-176 RG18/18 A1883c0006 04INS000171C230 Journal of Macromolecular Science, Part A: Pure and Applied Chemistry © 2021 Taylor & Francis Group, LLC. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1080/10601325.2021.1984849. application/pdf |
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Science::Chemistry Polythioethers Polysulfonium Polyelectrolytes Stuparu, Mihaiela Corina Khan, Anzar Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
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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. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Stuparu, Mihaiela Corina Khan, Anzar |
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Stuparu, Mihaiela Corina Khan, Anzar |
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Stuparu, Mihaiela Corina |
title |
Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
title_short |
Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
title_full |
Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
title_fullStr |
Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
title_full_unstemmed |
Poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
title_sort |
poly(ß-hydroxy thioether)s: synthesis through thiol-epoxy ‘click’ reaction and post-polymerization modification to main-chain polysulfonium salts |
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2023 |
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https://hdl.handle.net/10356/172347 |
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