Configurationally Chiral SuFEx-Based Polymers

Dong Dong Liang, Sidharam P. Pujari, Muthusamy Subramaniam, Maarten Besten, Han Zuilhof*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

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 languageEnglish
Article numbere202116158
JournalAngewandte Chemie - International Edition
Volume61
Issue number8
Early online date17 Dec 2021
DOIs
Publication statusPublished - 14 Feb 2022

Keywords

  • Chiral Polymer
  • Click Chemistry
  • Enantiospecific
  • Polysulfonimidates
  • SuFEx Reaction

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