Facile synthesis of terrylene and its isomer benzoindenoperylene

3-(1-Naphthyl)perylene was synthesised by a palladium-catalysed cross-coupling reaction of 3-bromoperylene and 1-naphthaleneboronic acid. Oxidative cyclodehydrogenation of 3-(1-naphthyl)perylene selectively afforded terrylene or its isomer, benzo[4,5]indeno[1,2,3-cd]perylene. The yield of terrylene, an important fluorophore for single molecular spectroscopy, was significantly improved in comparison to literature methods. Benzoindenoperylene has an absorption maximum at 508 nm and shows no fluorescence in contrast to terrylene.