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Thiyl radical induced cis/trans isomerism in double bond containing elastomers
This report presents an evaluation of thiyl radical-induced cis/trans isomerism in double bond-containing elastomers, such as natural, polychloroprene, and polybutadiene rubbers. The study aims to extensively investigate structural changes in polymers after functionalisation using thiol–ene chemistr...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10413178/ https://www.ncbi.nlm.nih.gov/pubmed/37577099 http://dx.doi.org/10.1039/d3ra04157c |
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author | Kaur, Anureet Gautrot, Julien E. Akutagawa, Keizo Watson, Douglas Bickley, Alan Busfield, James J. C. |
author_facet | Kaur, Anureet Gautrot, Julien E. Akutagawa, Keizo Watson, Douglas Bickley, Alan Busfield, James J. C. |
author_sort | Kaur, Anureet |
collection | PubMed |
description | This report presents an evaluation of thiyl radical-induced cis/trans isomerism in double bond-containing elastomers, such as natural, polychloroprene, and polybutadiene rubbers. The study aims to extensively investigate structural changes in polymers after functionalisation using thiol–ene chemistry, a useful click reaction for modifying polymers and developing materials with new functionalities. The paper reports on the use of different thiols, and cis/trans isomerism was detected through (1)H NMR analysis, even at very low alkene/thiol mole ratios. The study finds that the configurational arrangements between non-functionalised elastomer units and thiolated units followed a trans-functionalised-cis units arrangement up to an alkene/thiol mole feed ratio of 0.3, while from 0.4 onward, a combination of trans-functionalised-cis and cis-functionalised-trans configurations are found. Additionally, it is observed that by increasing the level of functionalisation, the glass transition temperature of the resulting modified elastomer also increases. Overall, this study provides valuable insights into the effects of thiol–ene chemistry on the structure and properties of elastomers and could have important implications for the development of new materials with enhanced functionality. |
format | Online Article Text |
id | pubmed-10413178 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-104131782023-08-11 Thiyl radical induced cis/trans isomerism in double bond containing elastomers Kaur, Anureet Gautrot, Julien E. Akutagawa, Keizo Watson, Douglas Bickley, Alan Busfield, James J. C. RSC Adv Chemistry This report presents an evaluation of thiyl radical-induced cis/trans isomerism in double bond-containing elastomers, such as natural, polychloroprene, and polybutadiene rubbers. The study aims to extensively investigate structural changes in polymers after functionalisation using thiol–ene chemistry, a useful click reaction for modifying polymers and developing materials with new functionalities. The paper reports on the use of different thiols, and cis/trans isomerism was detected through (1)H NMR analysis, even at very low alkene/thiol mole ratios. The study finds that the configurational arrangements between non-functionalised elastomer units and thiolated units followed a trans-functionalised-cis units arrangement up to an alkene/thiol mole feed ratio of 0.3, while from 0.4 onward, a combination of trans-functionalised-cis and cis-functionalised-trans configurations are found. Additionally, it is observed that by increasing the level of functionalisation, the glass transition temperature of the resulting modified elastomer also increases. Overall, this study provides valuable insights into the effects of thiol–ene chemistry on the structure and properties of elastomers and could have important implications for the development of new materials with enhanced functionality. The Royal Society of Chemistry 2023-08-10 /pmc/articles/PMC10413178/ /pubmed/37577099 http://dx.doi.org/10.1039/d3ra04157c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Kaur, Anureet Gautrot, Julien E. Akutagawa, Keizo Watson, Douglas Bickley, Alan Busfield, James J. C. Thiyl radical induced cis/trans isomerism in double bond containing elastomers |
title | Thiyl radical induced cis/trans isomerism in double bond containing elastomers |
title_full | Thiyl radical induced cis/trans isomerism in double bond containing elastomers |
title_fullStr | Thiyl radical induced cis/trans isomerism in double bond containing elastomers |
title_full_unstemmed | Thiyl radical induced cis/trans isomerism in double bond containing elastomers |
title_short | Thiyl radical induced cis/trans isomerism in double bond containing elastomers |
title_sort | thiyl radical induced cis/trans isomerism in double bond containing elastomers |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10413178/ https://www.ncbi.nlm.nih.gov/pubmed/37577099 http://dx.doi.org/10.1039/d3ra04157c |
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