New classes of functionalized parylenes and poly(phenylene vinylene)s via coupling of dihaloxylyl diesters

New classes of poly(p-xylylene)s and poly(p-phenylene vinylene)s were synthesized and studied. The novel polymers differ from known variants of their kind in that the ethylene and vinylene repeat units are outfitted with ester groups, which can be readily modified through transesterification. The polymers were prepared by treating an appropriate dihalobenzene diester with either a reductant to afford the corresponding poly(p-xylylene) or a base to afford the corresponding poly(p-phenylene vinylene). Variation of the ester groups enabled a broad range of functional polymers to be prepared, including derivatives that are liquid crystalline, photoswitchable, water soluble or amenable to cycloaddition chemistry.