Cargando…
Intrinsically Re-curable Photopolymers Containing Dynamic Thiol-Michael Bonds
[Image: see text] The development of photopolymers that can be depolymerized and subsequently re-cured using the same light stimulus presents a significant technical challenge. A bio-sourced terpenoid structure, l-carvone, inspired the creation of a re-curable photopolymer in which the orthogonal re...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9264357/ https://www.ncbi.nlm.nih.gov/pubmed/35749449 http://dx.doi.org/10.1021/jacs.2c03525 |
_version_ | 1784742959814541312 |
---|---|
author | Stubbs, Connor J. Khalfa, Anissa L. Chiaradia, Viviane Worch, Joshua C. Dove, Andrew P. |
author_facet | Stubbs, Connor J. Khalfa, Anissa L. Chiaradia, Viviane Worch, Joshua C. Dove, Andrew P. |
author_sort | Stubbs, Connor J. |
collection | PubMed |
description | [Image: see text] The development of photopolymers that can be depolymerized and subsequently re-cured using the same light stimulus presents a significant technical challenge. A bio-sourced terpenoid structure, l-carvone, inspired the creation of a re-curable photopolymer in which the orthogonal reactivity of an irreversible thioether and a dynamic thiol-Michael bond enables both photopolymerization and thermally driven depolymerization of mechanically robust polymer networks. The di-alkene containing l-carvone was partially reacted with a multi-arm thiol to generate a non-crosslinked telechelic photopolymer. Upon further UV exposure, the photopolymer crosslinked into a mechanically robust network featuring reversible Michael bonds at junction points that could be activated to revert, or depolymerize, the network into a viscous telechelic photopolymer. The regenerated photopolymer displayed intrinsic re-curability over two recycles while maintaining the desirable thermomechanical properties of a conventional network: insolubility, resistance to stress relaxation, and structural integrity up to 170 °C. Our findings present an on-demand, re-curable photopolymer platform based on a sustainable feedstock. |
format | Online Article Text |
id | pubmed-9264357 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-92643572022-07-09 Intrinsically Re-curable Photopolymers Containing Dynamic Thiol-Michael Bonds Stubbs, Connor J. Khalfa, Anissa L. Chiaradia, Viviane Worch, Joshua C. Dove, Andrew P. J Am Chem Soc [Image: see text] The development of photopolymers that can be depolymerized and subsequently re-cured using the same light stimulus presents a significant technical challenge. A bio-sourced terpenoid structure, l-carvone, inspired the creation of a re-curable photopolymer in which the orthogonal reactivity of an irreversible thioether and a dynamic thiol-Michael bond enables both photopolymerization and thermally driven depolymerization of mechanically robust polymer networks. The di-alkene containing l-carvone was partially reacted with a multi-arm thiol to generate a non-crosslinked telechelic photopolymer. Upon further UV exposure, the photopolymer crosslinked into a mechanically robust network featuring reversible Michael bonds at junction points that could be activated to revert, or depolymerize, the network into a viscous telechelic photopolymer. The regenerated photopolymer displayed intrinsic re-curability over two recycles while maintaining the desirable thermomechanical properties of a conventional network: insolubility, resistance to stress relaxation, and structural integrity up to 170 °C. Our findings present an on-demand, re-curable photopolymer platform based on a sustainable feedstock. American Chemical Society 2022-06-24 2022-07-06 /pmc/articles/PMC9264357/ /pubmed/35749449 http://dx.doi.org/10.1021/jacs.2c03525 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Stubbs, Connor J. Khalfa, Anissa L. Chiaradia, Viviane Worch, Joshua C. Dove, Andrew P. Intrinsically Re-curable Photopolymers Containing Dynamic Thiol-Michael Bonds |
title | Intrinsically
Re-curable Photopolymers Containing
Dynamic Thiol-Michael Bonds |
title_full | Intrinsically
Re-curable Photopolymers Containing
Dynamic Thiol-Michael Bonds |
title_fullStr | Intrinsically
Re-curable Photopolymers Containing
Dynamic Thiol-Michael Bonds |
title_full_unstemmed | Intrinsically
Re-curable Photopolymers Containing
Dynamic Thiol-Michael Bonds |
title_short | Intrinsically
Re-curable Photopolymers Containing
Dynamic Thiol-Michael Bonds |
title_sort | intrinsically
re-curable photopolymers containing
dynamic thiol-michael bonds |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9264357/ https://www.ncbi.nlm.nih.gov/pubmed/35749449 http://dx.doi.org/10.1021/jacs.2c03525 |
work_keys_str_mv | AT stubbsconnorj intrinsicallyrecurablephotopolymerscontainingdynamicthiolmichaelbonds AT khalfaanissal intrinsicallyrecurablephotopolymerscontainingdynamicthiolmichaelbonds AT chiaradiaviviane intrinsicallyrecurablephotopolymerscontainingdynamicthiolmichaelbonds AT worchjoshuac intrinsicallyrecurablephotopolymerscontainingdynamicthiolmichaelbonds AT doveandrewp intrinsicallyrecurablephotopolymerscontainingdynamicthiolmichaelbonds |