The synthesis of graphene nanostructures using molecular chemistry promises a higher level of control than that offered by other methods. However, this approach is challenging due to the large number of aromatic rings that must be selectively fused into the desired structure, and for this purpose there is a shortage of suitable synthetic methods. The Scholl cyclodehydrogenation reaction is, to date, the most heavily used method for nanographene synthesis. Despite the general utility of the transition metal mediated [2+2+2] cycloaddition reaction for the formation of aromatic rings, it has been underutilized for nanographene synthesis. The focus of this project is to develop a sequential [2+2+2] / cyclodehydrogenation approach that will allow synthesis of diverse graphene nanostructures. A systematic screening effort allowed the identification of three effective [2+2+2] catalysts, based on Ni, Rh, and Ir. The most promising of these catalysts (Ni(COD)2 / 4 PPh3) was used for the synthesis of three functionalized triphenylenes, one of which was shown to be an effective precursor to a model nanographene.

Toward a general route to nanographenes via a [2+2+2] / cyclodehydrogenation sequence

2019 Spring National Meeting

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