Although enol ethers are widely used as quenching reagents for Grubbs catalysts, we discovered that cyclic enol ethers can be surprisingly effective monomers for ring-opening metathesis polymerization (ROMP) using Grubbs catalysts, resulting in poly(enol ether)s with perfect regioregularity and tunable molecular weights. These poly(enol ether)s are stable under basic or neutral conditions, but rapidly degrade into small molecules under acidic conditions or depolymerize back to monomer at moderately increased temperatures in the presence of Grubbs catalysts. Copolymerization of cyclic enol ether with norbornene-based monomers results in degradable polymers with evenly distributed degradable linkages, low dispersity, and a wide range of tunable physical properties. This simple method offers exciting opportunities to develop degradable polymers with tunable degradation rates, physical properties, and functions.

Degradable ROMP polymers from previously deemed catalyst-deactivating enol ethers

ACS Spring 2022

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