Ring-Opening Metathesis Polymerization of Tertiary Amide Monomers Derived from a Biobased Oxanorbornene

Abstract

Ring-opening metathesis polymerization (ROMP) of biobased oxanorbornene amides by Grubbs second generation catalyst was used to prepare a range of well-defined homo- and copolymers. A series of 11 amide monomers, featuring a variety of functionalities including amino acids and peptides, have been synthesized from a biobased oxanorbornene acid, prepared through the 100% atom economical tandem Diels–Alder lactonization between itaconic anhydride and furfuryl alcohol. The polymerization has been shown to be well-controlled, with the prepared homo- and copolymers possessing controlled molecular weights with narrow polydispersities.