Poly(p-fluoranthene vinylene)

Significance

The synthesis of a poly(arylene vinylene) composed entirely of fluoranthene-based repeat units is presented. For this purpose, the dithiocarbamate precursor route previously developed by Vanderzande and coworkers (Polymer 2006, 47, 123-131) was employed. The requisite monomers were prepared by aldol condensation of acenaphthenequinone (a well-precedented method for the synthesis of such hydrocarbons), followed by installation of the dithiocarbamate groups (see scheme). Anionic polymerization yielded relatively high-molecular weight, soluble precursor polymer 1. Films of 1 underwent efficient thermal elimination of the dithiocarbamate moiety in the solid state to yield the desired conjugated polymer, as demonstrated by in situ IR and UV-Vis spectroscopy. Cyclic voltammetry indicated that the poly(fluoranthene vinylene) behaves as an n-type semiconductor.