Regioselective Bromination and Functionalization of Dibenzo[hi,st]ovalene as Highly Luminescent Nanographene with Zigzag Edges.

Dibenzo[hi,st]ovalene (DBOV) is a nanographene with a combination of zigzag and armchair edges, consisting of 38 sp2 carbons. Excellent optical properties with strong red emission have been demonstrated. Here we report the regioselective bromination of DBOV bearing two mesityl groups (DBOV-Mes) by treatment with N-bromosuccinimide (NBS) under mild conditions. The dibrominated DBOV was further subjected to transition-metal-catalyzed cross-coupling reactions, that is, Suzuki and Sonogashira coupling, demonstrating the edge-decoration of DBOV with different functional groups. Notably, DBOVs arylated at the bay regions showed intense red emission and enhanced fluorescence quantum yields of up to 0.97. Amphoteric reduction and oxidation behavior were observed by cyclic voltammetry (CV) measurements. Chemical oxidation to stable radical cation species was also demonstrated, followed by reduction back to their neutral species.