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C3‑Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes

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posted on 01.02.2013, 00:00 by Tao Wang, Yu-Fei Zhang, Qin-Qing Hou, Wen-Rong Xu, Xiao-Ping Cao, Hak-Fun Chow, Dietmar Kuck
Based on a regioselective tris-formylation of a tribenzotriquinacene (TBTQ) hydrocarbon, the racemic C3-symmetrical TBTQ-trialdehyde and the corresponding TBTQ-trimethanol were synthesized along with their C1-isomers. Conversion of the C3-trialdehyde to three diastereomeric TBTQ-based cryptophanes occurring in high yield enabled the preparation of the optically pure C3-symmetrical TBTQ-trialdehydes and the determination of their absolute configuration. The racemic C3-symmetrical TBTQ-trimethanol was found to form several stable nanotubular aggregates in the solid state.