Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization

[Image: see text] Butenolides are a class of 5-membered lactones that hold great potential as bio-based monomers to replace oil-derived acrylates, of which they are cyclic analogues. Despite this structural resemblance, the reactivity of the unsaturated ester moiety of electron-poor butenolides lean...

Descripción completa

Detalles Bibliográficos
Autores principales: Lepage, Mathieu L., Alachouzos, Georgios, Hermens, Johannes G. H., Elders, Niels, van den Berg, Keimpe J., Feringa, Ben L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10416300/
https://www.ncbi.nlm.nih.gov/pubmed/37498188
http://dx.doi.org/10.1021/jacs.3c04314
_version_ 1785087742711955456
author Lepage, Mathieu L.
Alachouzos, Georgios
Hermens, Johannes G. H.
Elders, Niels
van den Berg, Keimpe J.
Feringa, Ben L.
author_facet Lepage, Mathieu L.
Alachouzos, Georgios
Hermens, Johannes G. H.
Elders, Niels
van den Berg, Keimpe J.
Feringa, Ben L.
author_sort Lepage, Mathieu L.
collection PubMed
description [Image: see text] Butenolides are a class of 5-membered lactones that hold great potential as bio-based monomers to replace oil-derived acrylates, of which they are cyclic analogues. Despite this structural resemblance, the reactivity of the unsaturated ester moiety of electron-poor butenolides leans toward that of maleic anhydride, another essential monomer that does not homopolymerize but copolymerizes in a highly alternating fashion with polarized electron-rich comonomers. By studying the reactivity of 5-methoxy and 5-acyloxy butenolides through a combination of kinetics and density functional theory (DFT) experiments, we explain why electron-poor butenolides constitute a missing link between acrylates and maleic anhydride in radical polymerization.
format Online
Article
Text
id pubmed-10416300
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-104163002023-08-12 Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization Lepage, Mathieu L. Alachouzos, Georgios Hermens, Johannes G. H. Elders, Niels van den Berg, Keimpe J. Feringa, Ben L. J Am Chem Soc [Image: see text] Butenolides are a class of 5-membered lactones that hold great potential as bio-based monomers to replace oil-derived acrylates, of which they are cyclic analogues. Despite this structural resemblance, the reactivity of the unsaturated ester moiety of electron-poor butenolides leans toward that of maleic anhydride, another essential monomer that does not homopolymerize but copolymerizes in a highly alternating fashion with polarized electron-rich comonomers. By studying the reactivity of 5-methoxy and 5-acyloxy butenolides through a combination of kinetics and density functional theory (DFT) experiments, we explain why electron-poor butenolides constitute a missing link between acrylates and maleic anhydride in radical polymerization. American Chemical Society 2023-07-27 /pmc/articles/PMC10416300/ /pubmed/37498188 http://dx.doi.org/10.1021/jacs.3c04314 Text en © 2023 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 Lepage, Mathieu L.
Alachouzos, Georgios
Hermens, Johannes G. H.
Elders, Niels
van den Berg, Keimpe J.
Feringa, Ben L.
Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization
title Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization
title_full Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization
title_fullStr Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization
title_full_unstemmed Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization
title_short Electron-Poor Butenolides: The Missing Link between Acrylates and Maleic Anhydride in Radical Polymerization
title_sort electron-poor butenolides: the missing link between acrylates and maleic anhydride in radical polymerization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10416300/
https://www.ncbi.nlm.nih.gov/pubmed/37498188
http://dx.doi.org/10.1021/jacs.3c04314
work_keys_str_mv AT lepagemathieul electronpoorbutenolidesthemissinglinkbetweenacrylatesandmaleicanhydrideinradicalpolymerization
AT alachouzosgeorgios electronpoorbutenolidesthemissinglinkbetweenacrylatesandmaleicanhydrideinradicalpolymerization
AT hermensjohannesgh electronpoorbutenolidesthemissinglinkbetweenacrylatesandmaleicanhydrideinradicalpolymerization
AT eldersniels electronpoorbutenolidesthemissinglinkbetweenacrylatesandmaleicanhydrideinradicalpolymerization
AT vandenbergkeimpej electronpoorbutenolidesthemissinglinkbetweenacrylatesandmaleicanhydrideinradicalpolymerization
AT feringabenl electronpoorbutenolidesthemissinglinkbetweenacrylatesandmaleicanhydrideinradicalpolymerization

Ejemplares similares