Configurationally Chiral SuFEx-Based Polymers
Novel methods to make synthetic chiral polymers are highly desirable given their potential in a rapidly increasing number of bio-inspired applications. The enantiospecific sulfur–fluorine exchange (SuFEx) reaction of chiral di-sulfonimidoyl fluorides (di-SFs) with diphenols, was used to produce high-molecular-weight chiral polymers with configurational backbone chirality. The resulting new class of polymers, polysulfonimidates, can be efficiently produced via this step-growth mechanism for a wide range of di-SFs and diphenols, yielding MnPS up to 283 kDa with a typical dispersity Đ around 1.6. The optical activity of the resulting chiral polymers is largely due to the intrinsic asymmetry of the S atoms (configurational chirality). Finally, the enantiospecificity (ee>98 %) of the polymerization reaction was demonstrated by the degradation of a disulfide-containing polysulfonimidate. This novel route towards configurational main-chain chirality opens up new approaches towards tailor-made chiral polymers with precisely defined properties.
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Format: | Article/Letter to editor biblioteca |
Language: | English |
Subjects: | Chiral Polymer, Click Chemistry, Enantiospecific, Polysulfonimidates, SuFEx Reaction, |
Online Access: | https://research.wur.nl/en/publications/configurationally-chiral-sufex-based-polymers |
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dig-wur-nl-wurpubs-5938062024-10-30 Liang, Dong Dong Pujari, Sidharam P. Subramaniam, Muthusamy Besten, Maarten Zuilhof, Han Article/Letter to editor Angewandte Chemie - International Edition 61 (2022) 8 ISSN: 1433-7851 Configurationally Chiral SuFEx-Based Polymers 2022 Novel methods to make synthetic chiral polymers are highly desirable given their potential in a rapidly increasing number of bio-inspired applications. The enantiospecific sulfur–fluorine exchange (SuFEx) reaction of chiral di-sulfonimidoyl fluorides (di-SFs) with diphenols, was used to produce high-molecular-weight chiral polymers with configurational backbone chirality. The resulting new class of polymers, polysulfonimidates, can be efficiently produced via this step-growth mechanism for a wide range of di-SFs and diphenols, yielding MnPS up to 283 kDa with a typical dispersity Đ around 1.6. The optical activity of the resulting chiral polymers is largely due to the intrinsic asymmetry of the S atoms (configurational chirality). Finally, the enantiospecificity (ee>98 %) of the polymerization reaction was demonstrated by the degradation of a disulfide-containing polysulfonimidate. This novel route towards configurational main-chain chirality opens up new approaches towards tailor-made chiral polymers with precisely defined properties. en application/pdf https://research.wur.nl/en/publications/configurationally-chiral-sufex-based-polymers 10.1002/anie.202116158 https://edepot.wur.nl/563965 Chiral Polymer Click Chemistry Enantiospecific Polysulfonimidates SuFEx Reaction https://creativecommons.org/licenses/by-nc-nd/4.0/ https://creativecommons.org/licenses/by-nc-nd/4.0/ Wageningen University & Research |
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Chiral Polymer Click Chemistry Enantiospecific Polysulfonimidates SuFEx Reaction Chiral Polymer Click Chemistry Enantiospecific Polysulfonimidates SuFEx Reaction |
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Chiral Polymer Click Chemistry Enantiospecific Polysulfonimidates SuFEx Reaction Chiral Polymer Click Chemistry Enantiospecific Polysulfonimidates SuFEx Reaction Liang, Dong Dong Pujari, Sidharam P. Subramaniam, Muthusamy Besten, Maarten Zuilhof, Han Configurationally Chiral SuFEx-Based Polymers |
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Novel methods to make synthetic chiral polymers are highly desirable given their potential in a rapidly increasing number of bio-inspired applications. The enantiospecific sulfur–fluorine exchange (SuFEx) reaction of chiral di-sulfonimidoyl fluorides (di-SFs) with diphenols, was used to produce high-molecular-weight chiral polymers with configurational backbone chirality. The resulting new class of polymers, polysulfonimidates, can be efficiently produced via this step-growth mechanism for a wide range of di-SFs and diphenols, yielding MnPS up to 283 kDa with a typical dispersity Đ around 1.6. The optical activity of the resulting chiral polymers is largely due to the intrinsic asymmetry of the S atoms (configurational chirality). Finally, the enantiospecificity (ee>98 %) of the polymerization reaction was demonstrated by the degradation of a disulfide-containing polysulfonimidate. This novel route towards configurational main-chain chirality opens up new approaches towards tailor-made chiral polymers with precisely defined properties. |
format |
Article/Letter to editor |
topic_facet |
Chiral Polymer Click Chemistry Enantiospecific Polysulfonimidates SuFEx Reaction |
author |
Liang, Dong Dong Pujari, Sidharam P. Subramaniam, Muthusamy Besten, Maarten Zuilhof, Han |
author_facet |
Liang, Dong Dong Pujari, Sidharam P. Subramaniam, Muthusamy Besten, Maarten Zuilhof, Han |
author_sort |
Liang, Dong Dong |
title |
Configurationally Chiral SuFEx-Based Polymers |
title_short |
Configurationally Chiral SuFEx-Based Polymers |
title_full |
Configurationally Chiral SuFEx-Based Polymers |
title_fullStr |
Configurationally Chiral SuFEx-Based Polymers |
title_full_unstemmed |
Configurationally Chiral SuFEx-Based Polymers |
title_sort |
configurationally chiral sufex-based polymers |
url |
https://research.wur.nl/en/publications/configurationally-chiral-sufex-based-polymers |
work_keys_str_mv |
AT liangdongdong configurationallychiralsufexbasedpolymers AT pujarisidharamp configurationallychiralsufexbasedpolymers AT subramaniammuthusamy configurationallychiralsufexbasedpolymers AT bestenmaarten configurationallychiralsufexbasedpolymers AT zuilhofhan configurationallychiralsufexbasedpolymers |
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