Degradable Redox-Responsive Polyolefins

We introduce the synthesis of long-chain aliphatic metathesis polymers containing trimethyl-locked benzoquinone (TMBQ) as a redox-responsive functional unit. Specifically, we demonstrate that this moiety, placed in each repeating unit within the polymer, enables the on-demand degradation of the polymer into small molecules upon the addition of a reductant such as Na2S2O4. Notably, the cleaved TMBQ unit is recovered with high purity, hereby facilitating the synthesis of recyclable redox polymers. Importantly, we expand the scope of possible applications by postpolymerization modification of the olefinic backbone with bromine and pentafluorophenyl motifs, affording redox polymers with tailored functional properties.