Contorted Naphtho- and Fluorenocoronenes: Syntheses and Properties of Polycyclic Aromatics beyond Benzo- and Thiophenocoronenes.

Selective oxidative cyclodehydrogenation reactions on olefins carrying larger aromatic units are described to offer modular access to contorted polyaromatics of naphtho- and fluorenocoronenes, which are more extended frameworks than the known benzocoronenes. The annulation proceeded regioselectively when more than one mode was possible, based either on electronic or steric effect. The single-crystal field-effect transistor based on one of the derivatives, dinaphtho[ a, d]coronene, gave a p-carrier mobility of 0.04 cm2/(V s) and on/off current ratio of 102-103.