Abstract
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.
Original language | English |
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Article number | e202116158 |
Journal | Angewandte Chemie - International Edition |
Volume | 61 |
Issue number | 8 |
Early online date | 17 Dec 2021 |
DOIs | |
Publication status | Published - 14 Feb 2022 |
Keywords
- Chiral Polymer
- Click Chemistry
- Enantiospecific
- Polysulfonimidates
- SuFEx Reaction
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CCDC 2114205: Experimental Crystal Structure Determination
Liang, D. D. (Creator), Pujari, S. P. (Creator), Subramaniam, M. (Creator), Besten, M. (Creator) & Zuilhof, H. (Creator), Wageningen University & Research, 2022
DOI: 10.5517/ccdc.csd.cc28z05g
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