The synthesis and STM/AFM imaging of 'Olympicene' benzo[cd]pyrenes

Abstract

H-Benzo[cd ]pyrene ('Olympicene') is a polyaromatic hydrocarbon and non-Kekulé fragment of graphene. A new synthetic method has been developed for the formation of 6H-benzo[cd]pyrene and related ketones including the first time isolation of the unstable alcohol 6H-benzo[cd]pyren-6-ol. Molecular imaging of the reaction products with scanning tunnelling microscopy (STM) and non-contact atomic force microscopy (NC-AFM) characterised the 6H-benzo[cd]pyrene as well as the previously intangible and significantly less stable 5 H-benzo[cd ]pyrene, the fully conjugated benzo[cd]pyrenyl radical and the ketones as oxidation products.