Corannulene

"Corannulene is a polycyclic aromatic hydrocarbon with chemical formula C₂₀H₁₀.^[1] The molecule consists of a cyclopentane ring fused with 5 benzene rings, so another name for it is [5]circulene. It is of scientific interest because it is a geodesic polyarene and can be considered a fragment of buckminsterfullerene. Due to this connection and also its bowl shape, corannulene is also known as a buckybowl. Corannulene exhibits a bowl-to-bowl inversion with an inversion barrier of 10.2 kcal/mol (42.7 kJ/mol) at −64 °C."

"The observed aromaticity for this compound is explained with a so-called annulene-within-an-annulene model. According to this model corannulene is made up of an aromatic 6 electron cyclopentadienyl anion surrounded by an aromatic 14 electron annulenyl cation. This model was suggested by Barth and Lawton in the first synthesis of corannulene in 1966.^[3] They also suggested the trivial name 'corannulene', which is derived from the annulene-within-an-annulene model: core + annulene."