Copolymerization of dibenzofuran and dichloromethane

As part of a project involving synthesis of model oligomers of coal derived asphaltenes and preasphaltenes, we required bis(2-dibenzofuranyl)methane (1). The successful preparation of 1 was carried out via coupling of 2-lithio-dibenzofuran with 2-formyldibenzofuran, followed by reduction of the resulting diaryl substituted methanol. Attempts to prepare 1 by Friedel-Crafts alkylation of dibenzofuran (DBF) with stoichiometric amounts of CH/sub 2/Cl/sub 2/ failed. However, when CH/sub 2/Cl/sub 2/ was present in excess (as solvent), alkylation of DBF proceeded smoothly at ambient temperature to yield an insoluble, infusible, yellow powder. We report herein preliminary observations on the characteristics and structural features of this new copolymer.