The design of narrow bandgap polymers remains a major challenge in the field of organic conductors. An alternative scheme is proposed for reducing the bandgap, namely the construction of a one-dimensional graphite-like chain. Terthienyl frozen in a fully planar syn conformation is used as a simplified model compound for rigidified polythiophene. Its synthesis, cyclic voltammetry results, and electropolymerization are reported, which suggest that even smaller bandgaps could be produced in polythiophenes using this strategy.