C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes

Wang T, Zhang Y-F, Hou Q-Q, Xu W-R, Cao X-P, Chow H-F, Kuck D (2013)
The Journal Of Organic Chemistry 78(3): 1062-1069.

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Abstract
Based on a regioselective tris-formylation of a tribenzotriquinacene (TBTQ) hydrocarbon, the racemic C-3-symmetrical TBTQ-trialdehyde and the corresponding TBTQ-trimethanol were synthesized along with their C-1-isomers. Conversion of the C-3-trialdehyde to three diastereomeric TBTQ-based cryptophanes occurring in high yield enabled the preparation of the optically pure C-3-symmetrical TBTQ-trialdehydes and the determination of their absolute configuration. The racemic C-3-symmetrical TBTQ-trimethanol was found to form several stable nanotubular aggregates in the solid state.
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Wang T, Zhang Y-F, Hou Q-Q, et al. C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes. The Journal Of Organic Chemistry. 2013;78(3):1062-1069.
Wang, T., Zhang, Y. - F., Hou, Q. - Q., Xu, W. - R., Cao, X. - P., Chow, H. - F., & Kuck, D. (2013). C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes. The Journal Of Organic Chemistry, 78(3), 1062-1069.
Wang, T., Zhang, Y. - F., Hou, Q. - Q., Xu, W. - R., Cao, X. - P., Chow, H. - F., and Kuck, D. (2013). C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes. The Journal Of Organic Chemistry 78, 1062-1069.
Wang, T., et al., 2013. C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes. The Journal Of Organic Chemistry, 78(3), p 1062-1069.
T. Wang, et al., “C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes”, The Journal Of Organic Chemistry, vol. 78, 2013, pp. 1062-1069.
Wang, T., Zhang, Y.-F., Hou, Q.-Q., Xu, W.-R., Cao, X.-P., Chow, H.-F., Kuck, D.: C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes. The Journal Of Organic Chemistry. 78, 1062-1069 (2013).
Wang, Tao, Zhang, Yu-Fei, Hou, Qm-Qing, Xu, Wen-Rong, Cao, Xiao-Ping, Chow, Hak-Fun, and Kuck, Dietmar. “C-3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes”. The Journal Of Organic Chemistry 78.3 (2013): 1062-1069.
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5 Citations in Europe PMC

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Tribenzotriquinacene receptors for C60  fullerene rotors: towards C3 symmetrical chiral stators for unidirectionally operating nanoratchets.
Bredenkotter B, Grzywa M, Alaghemandi M, Schmid R, Herrebout W, Bultinck P, Volkmer D., Chemistry 20(29), 2014
PMID: 24965605
Selective host molecules obtained by dynamic adaptive chemistry.
Matache M, Bogdan E, Hadade ND., Chemistry 20(8), 2014
PMID: 24470060
Unidirectional molecular stacking of tribenzotriquinacenes in the solid state: a combined X-ray and theoretical study.
Brandenburg JG, Grimme S, Jones PG, Markopoulos G, Hopf H, Cyranski MK, Kuck D., Chemistry 19(30), 2013
PMID: 23766137

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