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Published on: February 19, 2016
C3-symmetrical tribenzotriquinacene derivatives: optical resolution through cryptophane synthesis and supramolecular
Tao Wang1, Yu-Fei Zhang, Qin-Qing Hou
1State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China.
Abstract:
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.
