PUB - Publikationen an der Universität Bielefeld

The synthesis of tribenzotriquinacenes (TBTQs) that bear three phenylethynyl groups at the peripheral positions of the bowl-shaped molecular scaffold has been achieved by use of different strategies. Although the C-1- and C-3-symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding C-1- and C-3-symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained in pure form. Threefold cyclocondensation of these TBTQ-based tris-tolanes with tetracyclone gave C-1- and C-3-tris(pentaphenylphenyl)tribenzotriquinacenes in good yields. Attempts to generate a completely closed graphene-like periphery around the TBTQ core by Scholl cyclodehydrogenation of the C-3-symmetrical isomer failed.