Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration

Kuck D, Linke J, Teichmann LC, Barth D, Tellenbroeker J, Gestmann D, Neumann B, Stammler H-G, Bögge H (2016)
PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18(17): 11722-11737.

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The solid-state molecular structure of centrohexaindane (1), a unique hydrocarbon comprising six benzene rings clamped to each other in three dimensions around a neopentane core, and the molecular packing in crystals of 1 center dot CHCl3 are reported. The molecular T-d-symmetry and the Cartesian orientation of the six indane wings of 1 in the solid state have been confirmed. The course and limitation of electrophilic aromatic substitution of 1 are demonstrated for the case of nitration. Based on nitration experiments of a lower congener of 1, tribenzotriquinacene 5, the six-fold nitrofunctionalisation of 1 has been achieved in excellent yield, giving four constitutional isomers, two nonsymmetrical (14 and 17) and two C-3-symmetrical ones (15 and 16), all of which contain one single nitro group in each of the six benzene rings. The relative yields of the four isomers (similar to 3 : 1 : 1 : 3) point to a random electrophilic attack of the electrophiles at the twelve formally equivalent outer positions of the aromatic periphery of 1, suggesting electronic independence of its six aromatic pi-electron systems. In turn, the pronounced conformational rigidity of the centrohexacyclic framework of 1 enables the unequivocal structural identification of the isomeric hexanitrocentrohexaindanes 14-17 by H-1 NMR spectroscopy.
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Kuck D, Linke J, Teichmann LC, et al. Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 2016;18(17):11722-11737.
Kuck, D., Linke, J., Teichmann, L. C., Barth, D., Tellenbroeker, J., Gestmann, D., Neumann, B., et al. (2016). Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 18(17), 11722-11737.
Kuck, D., Linke, J., Teichmann, L. C., Barth, D., Tellenbroeker, J., Gestmann, D., Neumann, B., Stammler, H. - G., and Bögge, H. (2016). Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18, 11722-11737.
Kuck, D., et al., 2016. Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 18(17), p 11722-11737.
D. Kuck, et al., “Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration”, PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 18, 2016, pp. 11722-11737.
Kuck, D., Linke, J., Teichmann, L.C., Barth, D., Tellenbroeker, J., Gestmann, D., Neumann, B., Stammler, H.-G., Bögge, H.: Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration. PHYSICAL CHEMISTRY CHEMICAL PHYSICS. 18, 11722-11737 (2016).
Kuck, Dietmar, Linke, Jens, Teichmann, Lisa Christin, Barth, Dieter, Tellenbroeker, Joerg, Gestmann, Detlef, Neumann, Beate, Stammler, Hans-Georg, and Bögge, Hartmut. “Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration”. PHYSICAL CHEMISTRY CHEMICAL PHYSICS 18.17 (2016): 11722-11737.
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