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Poly(p-phenylene sulfide) (PPS) is a highly robust thermoplastic with outstanding thermal and chemical stability. However, development of functional PPS-based materials is hampered by harsh synthetic conditions and poor solubility. As an alternative to nucleophilic aromatic substitution (S_NAr), we report herein on the use of benzoquinone conjugate addition chemistry to prepare PPS derivatives bearing redox-active hydroquinones in the polymer backbone. Specifically, we utilize thiosilanes as thiol surrogates to attenuate unproductive redox isomerization reactions and to provide a thermodynamic driving force for polymerization. The silyl transfer conjugate addition process results in a poly(phenylene silylhydroquinone sulfide) (PPSHS) amenable to several divergent modes of functionalization. Notably, the so-formed PPSHS exists as gels, which swell organic solvents and exhibit distinct changes in color and …