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A facile synthesis of elusive alkoxy-substituted hexa-peri-hexabenzocoronene.

Oxidative cyclodehydrogenation of hexakis(4-alkoxyphenyl)benzene produces a quantitative yield of an indenofluorene derivative rather than the expected alkoxy-substituted hexa-peri-hexabenzocoronene (HBC). The structure of the unexpected indenofluorene was established by X-ray crystallography. The mechanistic considerations for the formation of the indenofluorene derivative led us to devise an alternative synthesis of elusive alkoxy-substituted HBC-a potentially important, disk-shaped structure for the preparation of liquid crystalline materials for practical applications in the emerging areas of molecular electronics and nanotechnology.