New arenemethylenes for the synthesis of low band gap polymers

Based on theoretical calculations, polyarenemethylenes I (PAM) have been predicted to be low polymers. The preparation of such a polymer with a well defined structure demands the synthesis of suitable precursors. We have been able to synthesize a variety of new monomers with alternating aromatic and quinoid subunits. We present here the synthesis of the unsymmetrical precursor 4 and the soluble precursor 8 which has been transfered into the dimer 9. Another possibility to introduce a solubility increasing function into the precursor is demonstrated at 11. Furthermore the precursor 14 with 2,3′-linking instead of 2,2′-linking between aromatic and quinoid unit has been synthesized. Compounds 14 shows electrochromic behavior.