Poly(iodostyrene) in an attractive material for post-polymerization modification to prepare styrenic polymers with diverse side chain functionality using cross-coupling reactions and polymer-supported hypervalent iodine reagents via oxidation. Prior efforts towards the synthesis of poly(iodostyrene) have relied upon direct iodination of pre-formed polystyrene substrates or the use of anionic polymerization systems. The direct substitution of iodine onto polystyrene requires harsh conditions, aggressive reagents and long reaction times which only result in up to 80% iodination and anionic polymerization of iodostyrene is complicated by undesirable halogen exchange and coupling reactions. We demonstrate the use of controlled radical polymerization techniques (i.e. RAFT and ATRP) for the synthesis of well-defined poly(4-iodostyrene) with low dispersity and predicable molar mass. Additionally, we show the utility of poly(4-iodostyrene) to prepare polymer-supported hypervalent iodine reagents and as a precursor for synthesizing functionalized polystyrenics using efficient cross-coupling chemistry.

Controlled radical polymerization of Iiodostyrene

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ACS Fall 2022

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