Radical Ring-Opening Polymerization of N-(Malonyloxy)phthalimide-Functionalized Vinylcyclopropane: Tuning Material Property via Selective Decarboxylation

Si-Qi Li; Ke Li; Dian-Feng Chen

doi:10.1002/cjoc.202400635

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (1) : 53 -60. DOI: 10.1002/cjoc.202400635

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Radical Ring-Opening Polymerization of N-(Malonyloxy)phthalimide-Functionalized Vinylcyclopropane: Tuning Material Property via Selective Decarboxylation

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Abstract

Comprehensive Summary:Post-polymerization modification provides an important approach to tuning the material properties of obtained polymers. In this work, we demonstrated a rational design of novel vinylcyclopropane monomer bearing a pendant N-hydroxylphthalimide redox ester, and explored its radical ring-opening polymerization behavior under visible-light conditions. Photochemical decarboxylation of resulted polymer provided unique access to poly(vinylcyclopropane) bearing single ester group in each repeating unit. This decarboxylative modification has greatly reshaped the thermal and mechanical properties, converting a glassy polymer into a soft, ductile, and rubber-like material.

Keywords

Vinylcyclopropane / N-(Malonyloxy)phthalimide / Radical ring-opening polymerization / Decarboxylation / Soft materials

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Si-Qi Li, Ke Li, Dian-Feng Chen. Radical Ring-Opening Polymerization of N-(Malonyloxy)phthalimide-Functionalized Vinylcyclopropane: Tuning Material Property via Selective Decarboxylation. Chinese Journal of Chemistry, 2025, 43(1): 53-60 DOI:10.1002/cjoc.202400635