Synthesis and Properties of Symmetric and Unsymmetric Dibenzothienopyrroles

Symmetrical and unsymmetrical heteroacenes containing thiophene and pyrrole rings were synthesized. The unsymmetrical heteroacene was synthesized in two steps involving an unexpected palladium catalyzed amination of alkyl or aryl amines with benzo[b]thiophene followed by a copper catalyzed coupling. The symmetrical heteroacene was obtained by a palladium catalyzed amination reaction and also by a copper catalyzed amidation reaction. The crystal structure, photophysical and electrochemical properties of symmetrical and unsymmetrical heteroacenes are described.