Thiol-triggered deconstruction of bifunctional silyl ether terpolymers via an S_NAr-triggered cascade.

ABSTRACT: While Si-containing polymers can often be deconstructed using chemical triggers such as fluoride, acids, and bases, they are resistant to cleavage by mild reagents such as biological nucleophiles, thus limiting their end-of-life options and potential environmental degradability. Here, using ring-opening metathesis polymerization, we synthesize terpolymers of (1) a "functional" monomer (e.g., a polyethylene glycol macromonomer or dicyclopentadiene); (2) a monomer containing an electrophilic pentafluorophenyl (PFP) substituent; and (3) a cleavable monomer based on a bifunctional silyl ether . Exposing these polymers to thiols under basic conditions triggers a cascade of nucleophilic aromatic substitution (S_NAr) at the PFP groups, which liberates fluoride ions, followed by c

SUBMITTER: Brown CM 

PROVIDER: S-EPMC10445473 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature