Hexa-peri-hexabenzocoronene with Different Acceptor Units for Tuning Optoelectronic Properties

Hexa-peri-hexabenzocoronene (HBC)-based donor–acceptor dyads were synthesized with three different acceptor units, through two pathways: 1) “pre-functionalization” of monobromo-substituted hexaphenylbenzene prior to the cyclodehydrogenation; and 2) “post-functionalization” of monobromo-substituted HBC after the cyclodehydrogenation. The HBC–acceptor dyads demonstrated varying degrees of intramolecular charge-transfer interactions, depending on the attached acceptor units, which allowed tuning of their photophysical and optoelectronic properties, including the energy gaps. The two synthetic pathways described here can be complementary and potentially be applied for the synthesis of nanographene–acceptor dyads with larger aromatic cores, including one-dimensionally extended graphene nanoribbons.