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.

Two saddle-shaped polycyclic aromatic compounds (8 a and 8 b) bearing an all-cis-[5.5.5.5]fenestrane core surrounded by an o,p,o,p,o,p,o,p-cyclooctaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. The key step of this synthesis involves the formation of four cycloheptatriene rings from the corresponding electron-rich 1,4,9,12-tetraarylfenestrindane derivatives 7 a and 7 b in Scholl-type cyclizations. The structural details of the D -symmetric saddle compound 8 a were determined by X-ray crystallography, and the properties of 8 a and 8 b were studied by UV/Vis and fluorescence spectroscopy and cyclic voltammetry.