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.

Single and triple bay-bridging Scholl-type cyclizations of several 1,4,8-triaryl-substituted tribenzotriquinacenes are subject to pronounced electronic and steric substituent effects.

The successful enlargement of the curved π-electron periphery of the wizard hat-shaped polycyclic aromatic compound 1 is described. The target structure 2 features an m,m,p,m,m,p,m,m,p-nonaphenylene belt fused to a central tribenzotriquinacene unit. The synthesis involves a multiple regioconvergent Scholl-type dehydrocyclization as the key step. Spectroscopic, structural, and electronic properties of the title compound 2 are reported.

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