Synthesis and polymerizability of 7,8-dicyano-7,8-diphenylquinodimethane

7,8-Dicyano-7,8-diphenylquinodimethane (DCDPQ) was prepared by oxidation of the dianion of α,α′-dicyano-α,α′-diphenylxylene. ¹H-NMR of a solution of the purified compound showed that the cis and trans isomers were present in a 1:1 ratio. Following further spectroscopic and electronic characterization the polymerizability of the title compound was investigated. DCDPQ did not homopolymerize at 65°C in the presence of AIBN. DCDPQ copolymerized with p-methoxystyrene and p-aminostyrene in the presence of AIBN at 65°C. Characterization of the latter two copolymers indicated that they were nearly alternating. The copolymerization between DCDPQ and p-aminostyrene proceeded in the absence of AIBN.