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A Twisted Chiral Cavitand with 5-Fold Symmetry and Its Length-Selective Binding Properties
Tan-Hao Shi1, Yuuya Nagata2, Shigehisa Akine3,4
1Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Abstract:
Controlling bottom-up syntheses from chiral seeds to construct architectures with specific chiralities is currently challenging. Herein, a twisted chiral cavitand with 5-fold symmetry was constructed by bottom-up synthesis using corannulene as the chiral seed and pillar[5]arene as the chiral wall. After docking between the seed and the wall, their dynamic chiralities (M and P) are fixed. Moreover, the formed hedges also exhibit M and P chirality. Through dynamic covalent bonding, the thermodynamically stable product is obtained selectively as a pair of enantiomers (MMM and PPP), where all three subcomponents, i.e., the corannulene, hedges, and pillar[5]arene, are tilted in the same direction. Furthermore, the twisted cavitand exhibits length-selective binding to alkylene dibromides, with three maximum binding constants being unexpectedly observed.
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