C3-Symmetrical Tribenzotriquinacene Derivatives: Optical Resolution through Cryptophane Synthesis and Supramolecular Self-Assembly into Nanotubes

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• 作者：Tao Wang ; Yu-Fei Zhang ; Qin-Qing Hou ; Wen-Rong Xu ; Xiao-Ping Cao ; Hak-Fun Chow ; Dietmar Kuck
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：February 1, 2013
• 年：2013
• 卷：78
• 期：3
• 页码：1062-1069
• 全文大小：472K
• 年卷期：v.78,no.3(February 1, 2013)
• ISSN：1520-6904

文摘

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.