Synthesis of a Carbon Nanocone by Cascade Annulation

More than 50 years have passed since the first observation of graphitic cones in the pyrolysis of carbon. However, to date there has been no report in the literature on the synthesis of such carbon allotropes. Here we present the first synthesis of a carbon nanocone, which comprises a pentagon encircled by 30 hexagons, by means of a palladium-catalyzed cross-coupling reaction. In this synthetic approach, 15 C–C bonds were constructed from a cone-shaped aromatic scaffold, corannulene, and five naphthalene dicarboximide moieties through a cascade of [3 + 3] and [4 + 2] annulations. The conical geometry of the first synthetic carbon nanocone was confirmed by X-ray crystallography. The optical and electronic properties of this graphitic cone were elucidated by UV/vis and fluorescence spectroscopy and cyclic voltammetry.