Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core

Mughal E, Neumann B, Stammler H-G, Kuck D (2014)
European Journal of Organic Chemistry (33): 7469-7480.

Journal Article | Published | English

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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 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.
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Mughal E, Neumann B, Stammler H-G, Kuck D. Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core. European Journal of Organic Chemistry. 2014;(33):7469-7480.
Mughal, E., Neumann, B., Stammler, H. - G., & Kuck, D. (2014). Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core. European Journal of Organic Chemistry(33), 7469-7480.
Mughal, E., Neumann, B., Stammler, H. - G., and Kuck, D. (2014). Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core. European Journal of Organic Chemistry, 7469-7480.
Mughal, E., et al., 2014. Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core. European Journal of Organic Chemistry, (33), p 7469-7480.
E. Mughal, et al., “Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core”, European Journal of Organic Chemistry, 2014, pp. 7469-7480.
Mughal, E., Neumann, B., Stammler, H.-G., Kuck, D.: Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core. European Journal of Organic Chemistry. 7469-7480 (2014).
Mughal, Ehsan, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “Tribenzotriquinacenes that Bear Three Peripheral Pentaphenylphenyl Residues: Steric Crowding at a Bowl-Shaped Core”. European Journal of Organic Chemistry 33 (2014): 7469-7480.
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