Tri-N-annulated hexarylene: an approach to well-defined graphene nanoribbons with large dipoles

A highly efficient synthetic methodology for tri-N-annulated hexarylenes from easily available N-annulated perylenes, which is favored by the oxidative ring fusion driven by DDQ/Sc[(OTf).sub.3] is reported. The combination of [pi]-[pi] stacking interactions and dipole-dipole interactions observed for the tri-N-annulated hexarylene dyes which exhibit remarkably large dipole moments might favor the formation of highly ordered supramolecular structures that result in enhanced charge carrier mobilities.