Novel bio-derivable tricyclic oxanorbornene polymers, based upon secondary furfurylamine and maleic anhydride derived monomers, prepared via ring opening metathesis polymerization (ROMP) are reported. The tricyclic oxanorbornenes with fused lactam ring are exo Diels–Alder adducts. DFT calculations support the cycloaddition is the first step, followed by lactamization. The polymerizations are rapid and deliver polymers with targeted molar mass and low dispersity (Đ). The prepared polymers with furanyl pendant groups have reactivity towards maleimide-bearing compounds to form thermally induced crosslinked networks through thermoreversible Diels–Alder reactions. The thermoreversible (self-healing) behavior is confirmed by sol gel transition. This new class of bio-derived polymer could be further modified with different active moieties as pendant groups and hence be tailored for more applications in the future.
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M. Naguib would like to thank the Cultural Affairs & Missions Sector of Egypt for financial support. D.J.K. acknowledges the Royal Society of Chemistry and the Faculty of Science and Engineering at the University of Wolverhampton for funding.
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Naguib, M., Rashed, A. & Keddie, D.J. Self-healing polymers synthesized by ring opening metathesis polymerization (ROMP) of bio-derived furanic molecules. J Mater Sci 56, 8900–8909 (2021). https://doi.org/10.1007/s10853-021-05853-x