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Shi, Tan-Hao; Nagata, Yuuya; Akine, Shigehisa; Ohtani, Shunsuke; Kato, Kenichi; Ogoshi, Tomoki
Journal of the American Chemical Society, 12/2022, Volume: 144, Issue: 51Journal Article
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 pillar5arene 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 pillar5arene, 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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