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Biomass-Derived Degradable Polymers via Alternating Ring-Opening Metathesis Polymerization of Exo-Oxanorbornenes and Cyclic Enol Ethers

  • Hao Sun*
    Hao Sun
    Department of Chemistry and Chemical & Biomedical Engineering, Tagliatela College of Engineering, University of New Haven, West Haven, Connecticut 06516, United States
    *Email: [email protected]
    More by Hao Sun
  • Tarek Ibrahim
    Tarek Ibrahim
    Department of Chemistry and Chemical & Biomedical Engineering, Tagliatela College of Engineering, University of New Haven, West Haven, Connecticut 06516, United States
  • Angelo Ritacco
    Angelo Ritacco
    Department of Chemistry and Chemical & Biomedical Engineering, Tagliatela College of Engineering, University of New Haven, West Haven, Connecticut 06516, United States
  • , and 
  • Katie Durkee
    Katie Durkee
    Department of Chemistry and Chemical & Biomedical Engineering, Tagliatela College of Engineering, University of New Haven, West Haven, Connecticut 06516, United States
    More by Katie Durkee
Cite this: ACS Macro Lett. 2023, 12, XXX, 1642–1647
Publication Date (Web):November 20, 2023
https://doi.org/10.1021/acsmacrolett.3c00608
© 2023 American Chemical Society

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    Abstract

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    Degradable polymers made via ring-opening metathesis polymerization (ROMP) hold tremendous promise as eco-friendly materials. However, most of the ROMP monomers are derived from petroleum resources, which are typically considered less sustainable compared to biomass. Herein, we present a synthetic strategy to degradable polymers by harnessing alternating ROMP of biomass-based cyclic olefin monomers including exo-oxanorbornenes and cyclic enol ethers. A library of well-defined poly(enol ether)s with modular structures, tunable glass transition temperatures, and controlled molecular weights was achieved, demonstrating the versatility of this approach. Most importantly, the resulting copolymers exhibit high degrees of alternation, rendering their backbones fully degradable under acidic conditions.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsmacrolett.3c00608.

    • Experimental methods and synthetic procedures; 1H and 13C NMR spectra of materials; GPC traces of the polymers; mass spectrum of the degradation products; DSC thermograms of copolymers (PDF)

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