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.