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<i>C</i><sub>3</sub>‑Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes

By Tao Wang (12008), Yu-Fei Zhang (548799), Qin-Qing Hou (1997554), Wen-Rong Xu (1743100), Xiao-Ping Cao (1743097), Hak-Fun Chow (198245) and Dietmar Kuck (1743103)


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

Topics: Pharmacology, Biotechnology, Infectious Diseases, Space Science, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, Physical Sciences not elsewhere classified, Information Systems not elsewhere classified, Conversion, Optical Resolution, Derivative, NanotubesBased, hydrocarbon, TBTQ, diastereomeric, regioselective, cryptophane, racemic, nanotubular aggregates, Tribenzotriquinacene, Cryptophane Synthesis, configuration, Supramolecular, preparation, tribenzotriquinacene, determination
Year: 2013
DOI identifier: 10.1021/jo302470v.s006
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Provided by: FigShare
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