Molecular and electronic structure, reduction and coordination abilities of a novel polycyclic aromatic hydrocarbon (PAH) having a planar naphtho-group fused to the corannulene bowl have been broadly investigated using a combination of theoretical and experimental tools. A direct comparison of naphtho[2,3-a]corannulene (C28H14, 1) with parent corannulene (C20H10, 2) revealed the effect of framework topology change on electronic properties and aromaticity of 1. The presence of two reduction steps was predicted theoretically and confirmed experimentally for 1. The products of the mono- and doubly-reduced napththocorannulene were synthesized using chemical reduction with Group 1 metals and crystallographically characterized. The structural consequences of adding one and two electrons to the carbon framework of 1 are analyzed. Changes in aromaticity and charge distribution stemming from the stepwise electron acquisition are discussed based on DFT computational study.

Adding planar handle to a carbon bowl: Structure, aromaticity and reduction chemistry of naphthocorannulene

256th National Meeting (2018)

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