Merging Tribenzotriquinacene and Triptycene

Lucchesini F, Grasse M, Neumann B, Stammler H-G, Tellenbroeker J, Kuck D (2016)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2016(16): 2828-2841.

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Abstract
The geometric and chemically related structural motifs of tribenzotriquinacene (TBTQ, 1) and triptycene (2) have been merged for the first time on the level of the parent hydrocarbons. A classical cyclodehydration strategy was used to synthesize 1,4-dimethoxytribenzotriquinacene 13 and convert it into the corresponding TBTQ-based para-benzoquinone 4. The Diels-Alder reaction of 4 with anthracene afforded anti-and syn-cycloadducts 22 and 23, respectively, in the ratio of 1: 3, which were transformed into dibenzo(triptyceno) triquinacene 5, a new parent polycyclic aromatic hydrocarbon, and derivatives 25-28. The structure of TBTQ-quinone 4 was also extended to give related 1,4-anthraquinone 32. The intriguing geometrical and structural aspects of the merged TBTQ-triptycene motif were examined by X-ray crystal analysis and molecular modeling with the aim to construct tris(triptyceno) triquinacenes, hypothetical analogues that are characterized by a deep molecular cavity.
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Lucchesini F, Grasse M, Neumann B, Stammler H-G, Tellenbroeker J, Kuck D. Merging Tribenzotriquinacene and Triptycene. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2016;2016(16):2828-2841.
Lucchesini, F., Grasse, M., Neumann, B., Stammler, H. - G., Tellenbroeker, J., & Kuck, D. (2016). Merging Tribenzotriquinacene and Triptycene. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016(16), 2828-2841.
Lucchesini, F., Grasse, M., Neumann, B., Stammler, H. - G., Tellenbroeker, J., and Kuck, D. (2016). Merging Tribenzotriquinacene and Triptycene. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2016, 2828-2841.
Lucchesini, F., et al., 2016. Merging Tribenzotriquinacene and Triptycene. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016(16), p 2828-2841.
F. Lucchesini, et al., “Merging Tribenzotriquinacene and Triptycene”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2016, 2016, pp. 2828-2841.
Lucchesini, F., Grasse, M., Neumann, B., Stammler, H.-G., Tellenbroeker, J., Kuck, D.: Merging Tribenzotriquinacene and Triptycene. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2016, 2828-2841 (2016).
Lucchesini, Francesco, Grasse, Michael, Neumann, Beate, Stammler, Hans-Georg, Tellenbroeker, Joerg, and Kuck, Dietmar. “Merging Tribenzotriquinacene and Triptycene”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2016.16 (2016): 2828-2841.
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