Abstract

[n]Circulene is a macrocyclic arene in which a central n-sided polygon is completely surrounded and fused with benzenoids.1 Only four members of this family, [5]circulene (or corannulene), [6]circulene (or coronene), [7]circulene, and [8]circulene have been prepared to date. The shapes of these circulenes change from a bowl ([5]circulene) through a plane ([6]circulene) to a saddle ([7]circulene).  

[7] and [8]circulene are basic structural units of theoretical three-dimensional carbon allotropes of negative curvature, which are known as Mackay crystals or carbon Schwarzites. The next [n]circulene to be synthesized is [9]circulene. This presentation will cover our recent studies toward synthesis of benzannulated [9]circulenes through the Scholl reaction using outward and inward strategies as shown in the figure below.

Reference:

1. a) J. H. Dopper.; H. Wynberg. Tetrahedron Lett. 1972, 13, 763; b) J. S. Siegel.; T. J. Seiders. Chem. Br. 1995, 31, 313;