RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry
Abstract The polymerization of vinyl methacrylate (VMA) allows the synthesis of polymers with pendant double bonds. When this polymerization was undertaken in the presence of 2‐cyanopropyl dithiobenzoate as reversible addition–fragmentation chain transfer agent, it led almost exclusively to vinylest...
Published in: | Journal of Polymer Science Part A: Polymer Chemistry |
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crwiley:10.1002/pola.26210 2024-06-02T07:57:45+00:00 RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry Yhaya, Firdaus Sutinah, Arlingga Gregory, Andrew M. Liang, Mingtao Stenzel, Martina H. 2012 http://dx.doi.org/10.1002/pola.26210 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.26210 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.26210 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of Polymer Science Part A: Polymer Chemistry volume 50, issue 19, page 4085-4093 ISSN 0887-624X 1099-0518 journal-article 2012 crwiley https://doi.org/10.1002/pola.26210 2024-05-03T11:29:36Z Abstract The polymerization of vinyl methacrylate (VMA) allows the synthesis of polymers with pendant double bonds. When this polymerization was undertaken in the presence of 2‐cyanopropyl dithiobenzoate as reversible addition–fragmentation chain transfer agent, it led almost exclusively to vinylester functional sidegroups, which were available for further reactions. The vinylester functionality could not be functionalized using common thiol‐ene catalysts, but could be activated using Candida antarctica lipase B (CAL‐B) (Novozyme 435). The reaction between PVMA and various thiols in N, N ‐dimethyl formamide in the presence of CAL‐B led exclusively to the formation of the anti‐Markovnikov product. The rate of reaction between PVMA and 1‐butanethiol was monitored using 1 H NMR. The reaction was complete within 72 h. Similar results were obtained with other small‐sized thiols such as 2‐mercaptoethanol, 3‐mercaptopropionic acid, and 2‐(trimethylsilyl)ethanethiol, while more bulky thiols, such as secondary thiols, thiols with long alkyl chains, and sterically demanding thiols, such as mono(6‐deoxy‐6‐mercapto)‐β‐cyclodextrin, only led to lower conversions. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of Polymer Science Part A: Polymer Chemistry 50 19 4085 4093 |
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Wiley Online Library |
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English |
description |
Abstract The polymerization of vinyl methacrylate (VMA) allows the synthesis of polymers with pendant double bonds. When this polymerization was undertaken in the presence of 2‐cyanopropyl dithiobenzoate as reversible addition–fragmentation chain transfer agent, it led almost exclusively to vinylester functional sidegroups, which were available for further reactions. The vinylester functionality could not be functionalized using common thiol‐ene catalysts, but could be activated using Candida antarctica lipase B (CAL‐B) (Novozyme 435). The reaction between PVMA and various thiols in N, N ‐dimethyl formamide in the presence of CAL‐B led exclusively to the formation of the anti‐Markovnikov product. The rate of reaction between PVMA and 1‐butanethiol was monitored using 1 H NMR. The reaction was complete within 72 h. Similar results were obtained with other small‐sized thiols such as 2‐mercaptoethanol, 3‐mercaptopropionic acid, and 2‐(trimethylsilyl)ethanethiol, while more bulky thiols, such as secondary thiols, thiols with long alkyl chains, and sterically demanding thiols, such as mono(6‐deoxy‐6‐mercapto)‐β‐cyclodextrin, only led to lower conversions. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 |
format |
Article in Journal/Newspaper |
author |
Yhaya, Firdaus Sutinah, Arlingga Gregory, Andrew M. Liang, Mingtao Stenzel, Martina H. |
spellingShingle |
Yhaya, Firdaus Sutinah, Arlingga Gregory, Andrew M. Liang, Mingtao Stenzel, Martina H. RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
author_facet |
Yhaya, Firdaus Sutinah, Arlingga Gregory, Andrew M. Liang, Mingtao Stenzel, Martina H. |
author_sort |
Yhaya, Firdaus |
title |
RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
title_short |
RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
title_full |
RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
title_fullStr |
RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
title_full_unstemmed |
RAFT polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
title_sort |
raft polymerization of vinyl methacrylate and subsequent conjugation via enzymatic thiol‐ene chemistry |
publisher |
Wiley |
publishDate |
2012 |
url |
http://dx.doi.org/10.1002/pola.26210 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.26210 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.26210 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of Polymer Science Part A: Polymer Chemistry volume 50, issue 19, page 4085-4093 ISSN 0887-624X 1099-0518 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/pola.26210 |
container_title |
Journal of Polymer Science Part A: Polymer Chemistry |
container_volume |
50 |
container_issue |
19 |
container_start_page |
4085 |
op_container_end_page |
4093 |
_version_ |
1800740955544879104 |