Organocatalyzed Synthesis and Degradation of Functionalized Poly(4-allyloxymethyl-β-propiolactone)s

Yeji Yu, Minseong Kim, Gue Seon Lee, Hyo Won Lee, Jeung Gon Kim, Byeong Su Kim

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


The chemical synthesis of degradable poly(β-hydroxyalkanoate) (PHA) produced by microorganisms allows the control of the solubility, crystallinity, hydrophobicity, degradability, thermal, and mechanical properties by introducing functionality on the side chain. Herein, we synthesized a PHA derivative containing a pendant allyl group via the anionic ring-opening polymerization of a 4-allyloxymethyl-β-propiolactone (AMPL) monomer, which was prepared via the carbonylation of allyl glycidyl ether. The AMPL monomer was subjected to various organocatalysts in bulk to yield poly(4-allyloxymethyl-β-propiolactone) (PAMPL) with controllable molecular weight and dispersity. The prepared PAMPL polymers were characterized via 1H and 13C NMR, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) analyses. A photoactivated thiol-ene reaction allowed the postpolymerization modification of PAMPLs with varying substituents. Functionalized PAMPL polymers degraded under chemical and thermal conditions, and importantly, cross-linked PAMPL films degraded during exposure to soil and seawater under a wide range of degradation kinetics. This study provides the future potentials of the chemically synthesized and functionalized PHA for replacing conventional petroleum-derived polymers.

Original languageEnglish
Pages (from-to)10903-10913
Number of pages11
Issue number23
Publication statusPublished - 2021 Dec 14

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF-2021R1A2C3004978).

Publisher Copyright:
© 2021 American Chemical Society.

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry


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