Imidazolyl-Substituted Benzo- and Naphthodithiophenes as Precursors for the Synthesis of Transient Open-Shell Quinoids.

The synthesis of three novel imidazolyl-substituted sulfur-containing heteroacenes is reported. These heteroacenes consisting of annelated benzo- and naphthothiophenes serve as precursors for the generation of open-shell quinoid heteroacenes by oxidation with alkaline ferric cyanide. Spectroscopic and computational experiments support the formation of reactive open-shell quinoids, which, however, quickly produce paramagnetic polymeric material.