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Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals

We report a novel method to synthesize degradable poly(vinyl ether)s with cleavable thioacetal bonds periodically arranged in the main chains using controlled cationic copolymerization of vinyl ethers with a 7‐membered cyclic thioacetal (7‐CTA) via degenerative chain transfer (DT) to the internal th...

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Autores principales: Uchiyama, Mineto, Murakami, Yukihiro, Satoh, Kotaro, Kamigaito, Masami
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107285/
https://www.ncbi.nlm.nih.gov/pubmed/36369911
http://dx.doi.org/10.1002/anie.202215021
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author Uchiyama, Mineto
Murakami, Yukihiro
Satoh, Kotaro
Kamigaito, Masami
author_facet Uchiyama, Mineto
Murakami, Yukihiro
Satoh, Kotaro
Kamigaito, Masami
author_sort Uchiyama, Mineto
collection PubMed
description We report a novel method to synthesize degradable poly(vinyl ether)s with cleavable thioacetal bonds periodically arranged in the main chains using controlled cationic copolymerization of vinyl ethers with a 7‐membered cyclic thioacetal (7‐CTA) via degenerative chain transfer (DT) to the internal thioacetal bonds. The thioacetal bonds, which are introduced into the main chain by cationic ring‐opening copolymerization of 7‐CTA with vinyl ethers, serve as in‐chain dormant species to allow homogeneous propagation of vinyl ethers for all internal segments to afford copolymers with controlled overall and segmental molecular weights. The obtained polymers can be degraded into low‐ and controlled‐molecular‐weight polymers with narrow molecular weight distributions via hydrolysis. Various vinyl ethers with hydrophobic, hydrophilic, and functional pendants are available. Finally, one‐pot synthesis of multiblock copolymers and their degradation into diblock copolymers are also achieved.
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spelling pubmed-101072852023-04-18 Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals Uchiyama, Mineto Murakami, Yukihiro Satoh, Kotaro Kamigaito, Masami Angew Chem Int Ed Engl Research Articles We report a novel method to synthesize degradable poly(vinyl ether)s with cleavable thioacetal bonds periodically arranged in the main chains using controlled cationic copolymerization of vinyl ethers with a 7‐membered cyclic thioacetal (7‐CTA) via degenerative chain transfer (DT) to the internal thioacetal bonds. The thioacetal bonds, which are introduced into the main chain by cationic ring‐opening copolymerization of 7‐CTA with vinyl ethers, serve as in‐chain dormant species to allow homogeneous propagation of vinyl ethers for all internal segments to afford copolymers with controlled overall and segmental molecular weights. The obtained polymers can be degraded into low‐ and controlled‐molecular‐weight polymers with narrow molecular weight distributions via hydrolysis. Various vinyl ethers with hydrophobic, hydrophilic, and functional pendants are available. Finally, one‐pot synthesis of multiblock copolymers and their degradation into diblock copolymers are also achieved. John Wiley and Sons Inc. 2022-12-07 2023-01-23 /pmc/articles/PMC10107285/ /pubmed/36369911 http://dx.doi.org/10.1002/anie.202215021 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Uchiyama, Mineto
Murakami, Yukihiro
Satoh, Kotaro
Kamigaito, Masami
Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals
title Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals
title_full Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals
title_fullStr Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals
title_full_unstemmed Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals
title_short Synthesis and Degradation of Vinyl Polymers with Evenly Distributed Thioacetal Bonds in Main Chains: Cationic DT Copolymerization of Vinyl Ethers and Cyclic Thioacetals
title_sort synthesis and degradation of vinyl polymers with evenly distributed thioacetal bonds in main chains: cationic dt copolymerization of vinyl ethers and cyclic thioacetals
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107285/
https://www.ncbi.nlm.nih.gov/pubmed/36369911
http://dx.doi.org/10.1002/anie.202215021
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