N-Triflylation Enables δ-Valerolactam-Epoxide Alternating Copolymerization.

Authors

Tao Lai, Shuotong Wang, Junpeng Zhao

Published in

ACS macro letters. Pages 597-602. Apr 27, 2025. Epub Apr 27, 2025.

Abstract

δ-Valerolactam (VL), a six-membered cyclic amide, is easily accessible but hardly polymerizable, unlike other-membered homologues. We have discovered that simple N-triflylation effectively activates VL for undergoing copolymerization with epoxides. The strong electron-withdrawing triflyl group allows mild organobases, in cooperation with triethyl borane and an alcohol initiator, to trigger the reaction at room temperature, affording strictly alternating poly(ester-sulfonamide) with controlled molar mass and low dispersity. The method is proven applicable to a variety of epoxides, regardless of polarity and bulkiness of the substituents, and the products exhibit good chemical degradability, thermal/enzymatic stability, and a wide range of glass transition temperatures. The study indicates that N-sulfonylation and ring-opening (alternating) copolymerization together may build up a versatile platform to support the design and construction of heteroatom-rich polymers using conventionally nonpolymerizable compounds.

PMID:
40287837
Bibliographic data and abstract were imported from PubMed on 27 Apr 2025.

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