Towards a perylene-containing nanohoop.

An octabenzo [12]cycloparaphenylene I (nanohoop) was prepd. in four steps as a potential precursor to a perylene-like cycloparaphenylene. Addn. of the lithium reagent derived from 1,4-dibromonaphthalene to 1,4-cyclohexanedione, O-methoxymethylation and isolation of the cis-dinaphthylcyclohexane, nickel-catalyzed macrocyclization, and acid- and microwave-mediated aromatization yielded I in 0.34% overall yield. The absorption and emission spectra of I and of its unaromatized precursor were obtained and compared. [on SciFinder(R)]