Post-polymerization modification (PPM) is a powerful strategy to access a wide breadth of material properties from a single polymer backbone. This approach has been largely limited to side-chain and end-group modification, which constrains accessible material properties. Little attention has been directed towards the modification of polymer backbone composition—referred to as polymer backbone metamorphosis—to produce dramatic property changes on demand. Through the utilization of sigmatropic rearrangements, polymer backbone metamorphosis of polyesters to polyolefins was achieved. The polyesters were synthesized by ring opening transesterification polymerization of ω-vinyllactones, providing the backbone structure to facilitate Ireland-Claisen rearrangement (ICR). We have shown the application of ICR conditions induce total rearrangement of polyesters into polyolefins with no observed degradation. Material properties and changes imparted through ICR will be discussed.

Polymer backbone metamorphosis of polyesters to polyolefins via the Ireland-Claisen rearrangement

ACS Spring Meeting 2021

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