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- Title
Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core.
- Authors
Mughal, Ehsan Ullah; Neumann, Beate; Stammler, Hans‐Georg; Kuck, Dietmar
- Abstract
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 C1- and C3-symmetrical triformyl, triethynyl and triiodo derivatives were inseparable by chromatography, the corresponding C1- and C3-symmetrical tris(phenylethynyl)tribenzotriquinacenes were obtained in pure form. Threefold cyclocondensation of these TBTQ-based tris-tolanes with tetracyclone gave C1- and C3-tris(pentaphenylphenyl)tribenzotriquinacenes in good yields. Attempts to generate a completely closed graphene-like periphery around the TBTQ core by Scholl cyclodehydrogenation of the C3-symmetrical isomer failed.
- Subjects
POLYCYCLIC aromatic hydrocarbons synthesis; ORGANIC synthesis; GRAPHENE synthesis; CHROMATOGRAPHIC analysis; ISOMER synthesis
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 33, p7469
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201402995