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.