Synthesis and characterization of an oligomeric conjugated metal-containing poly(p-phenylenevinylene) analogue

A new nickel-containing bis(bromobenzyl)salphen monomer suitable for Gilch polymerization was prepared. Reaction with KO(t)Bu in THF-DMF afforded primarily gels, but also soluble, conjugated oligomers that are red-shifted in the absorption spectrum when compared to the monomer. This spectral change, consistent with an enhanced conjugation length, was also compared with a suitable model compound for the polymer. Our results indicate that Gilch polymerization may be a useful route to fully conjugated metal-containing polymers if attention is paid to ensuring solubility of the product.