Investigations on the configuration of new arenemethylenes for the synthesis of low bandgap polymers

The new arenemethylenes 9 and 13 have been synthesized by a Knoevenagel-type condensation, as precursor molecules for polyarenemethylenes (PAMs, 1) which are, based on theoretical calculations, low bandgap polymers. The configuration of the monomers was investigated, because this is a criterion to determine whether an electrochemical polymerization of the compounds could lead to linear polymers. All of the annulated polyarenemethylidenes 1 have a Z,Z-configuration, using the methods of preparation shown.