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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Main Authors: Liang, Dong Dong, Pujari, Sidharam P., Subramaniam, Muthusamy, Besten, Maarten, Zuilhof, Han
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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spelling 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
institution WUR NL
collection DSpace
country Países bajos
countrycode NL
component Bibliográfico
access En linea
databasecode dig-wur-nl
tag biblioteca
region Europa del Oeste
libraryname WUR Library Netherlands
language English
topic Chiral Polymer
Click Chemistry
Enantiospecific
Polysulfonimidates
SuFEx Reaction
Chiral Polymer
Click Chemistry
Enantiospecific
Polysulfonimidates
SuFEx Reaction
spellingShingle 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
description 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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