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A Single-Atom Upgrade to Polydicyclopentadiene

  • Benjamin Godwin
    Benjamin Godwin
    Department of Chemistry, University of Victoria, Victoria, British Columbia V8W 3V6, Canada
  • Monir H. Anvari
    Monir H. Anvari
    Department of Chemistry, University of British Columbia, Kelowna, British Columbia V1V 1V7, Canada
  • Tina Olfatbakhsh
    Tina Olfatbakhsh
    Materials and Manufacturing Research Institute (MMRI), University of British Columbia, Kelowna, British Columbia V1V 1V7, Canada
  • Mahshid Mahbod
    Mahshid Mahbod
    Materials and Manufacturing Research Institute (MMRI), University of British Columbia, Kelowna, British Columbia V1V 1V7, Canada
  • Abbas S. Milani
    Abbas S. Milani
    Materials and Manufacturing Research Institute (MMRI), University of British Columbia, Kelowna, British Columbia V1V 1V7, Canada
  • Gino A. DiLabio*
    Gino A. DiLabio
    Department of Chemistry, University of British Columbia, Kelowna, British Columbia V1V 1V7, Canada
    *Email: [email protected]
  • , and 
  • Jeremy E. Wulff*
    Jeremy E. Wulff
    Department of Chemistry, University of Victoria, Victoria, British Columbia V8W 3V6, Canada
    Centre for Advanced Materials and Related Technology (CAMTEC), University of Victoria, Victoria, British Columbia V8W 2Y2, Canada
    Department of Chemistry, University of Bath, Bath BA2 7AY, United Kingdom
    *Email: [email protected]
Cite this: Macromolecules 2023, 56, 4, 1592–1600
Publication Date (Web):February 8, 2023
https://doi.org/10.1021/acs.macromol.2c02260
Copyright © 2023 American Chemical Society

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    Abstract

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    Chemical cross-links within polymers increase mechanical strength and rigidity. Such cross-links can be either irreversible (e.g., those derived from carbon–carbon bonds) or reversible (e.g., those that depend on X–H···O hydrogen bonds). Here we describe a ketone-functionalized derivative of polydicyclopentadiene that establishes an unprecedented network of vinyl C–H···O hydrogen bonds within the polymer. The resulting thermoset displays a significantly increased glass transition temperature relative to the unfunctionalized polymer, together with enhancements to storage modulus, Young’s modulus, and compression strength.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.macromol.2c02260.

    • Complete experimental details including synthesis and polymerization protocols, spectra for monomers, and polymers, and thermal and mechanical testing data (PDF)

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