<i>C</i><sub>3</sub>‑Symmetrical
Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane
Synthesis and Supramolecular Self-Assembly into Nanotubes
- Publication date
- 2013
- Publisher
Abstract
Based on a regioselective tris-formylation of a tribenzotriquinacene
(TBTQ) hydrocarbon, the racemic <i>C</i><sub>3</sub>-symmetrical
TBTQ-trialdehyde and the corresponding TBTQ-trimethanol were synthesized
along with their <i>C</i><sub>1</sub>-isomers. Conversion
of the <i>C</i><sub>3</sub>-trialdehyde to three diastereomeric
TBTQ-based cryptophanes occurring in high yield enabled the preparation
of the optically pure <i>C</i><sub>3</sub>-symmetrical TBTQ-trialdehydes
and the determination of their absolute configuration. The racemic <i>C</i><sub>3</sub>-symmetrical TBTQ-trimethanol was found to
form several stable nanotubular aggregates in the solid state