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

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.