Three-Fold Scholl-Type Cycloheptatriene Ring Formation around a Tribenzotriquinacene Core: Toward Warped Graphenes

A nonplanar
polycyclic aromatic compound 6 bearing
a tribenzotriquinacene (TBTQ) core merged with an o,p,o,p,o,p-hexaphenylene belt was prepared and characterized by NMR spectroscopy
and X-ray crystallography. The key synthesis step involves three Scholl-type
cycloheptatriene ring formation steps of the 1,4,8-tris­(3′,4′-dimethoxyphenyl)-TBTQ
derivative 5. The bridging of each of the three TBTQ
bays by 1,2-phenylene units in compound 6 gives rise
to an unusual wizard hat shaped structure, which represents a promising
key intermediate for the construction of nonplanar nanographene molecules
bearing a TBTQ core.