Synthesis and characterization of polyacene precursors

Polyacenes are one-dimensional analogs of graphite and are predicted to have high conductivities without chemical doping.. The acid-catalyzed condensation of 1,2-bis(methoxymethyl)benzene gives a network polymer with idealized structure that corresponds to a linear polyacene precursor, that after elimination of H2, should yield polyacenes with extended π electron systems. In contrast, the polymerization, of 1,4-bis(methoxymethyl)benzene and 1,3-bis(methoxymethyl)benzene are expected to result in networks with a proportionately higher polybenzyl content. Based on TGA and IR studies, we propose that polyacene precursors are formed in the polymerization of the ortho substituted monomer, while the meta and para-substituted monomers contain a higher fraction of the less stable polybenzyl structure. Samples heated in an inert atmosphere show conversion of the acene precursors to partially graphitized products.