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Concyclic CH-π arrays for single-axis rotations of a bowl in a tube

Author

Listed:
  • Taisuke Matsuno

    (The University of Tokyo
    JST, ERATO, Isobe Degenerate π-Integration Project)

  • Masahiro Fujita

    (Tohoku University)

  • Kengo Fukunaga

    (The University of Tokyo)

  • Sota Sato

    (The University of Tokyo
    JST, ERATO, Isobe Degenerate π-Integration Project)

  • Hiroyuki Isobe

    (The University of Tokyo
    JST, ERATO, Isobe Degenerate π-Integration Project)

Abstract

The hydrogen bond is undoubtedly one of the most important non-covalent interactions. Among the several types of the hydrogen bonds, the CH–π interaction is a relatively new notion that is being recognised in chemistry and biology. Although the CH–π hydrogen bond and conventional hydrogen bonds share common features such as directionality, this weak interaction has played a secondary role in molecular recognition. In this study, we have devised a host–guest complex that is assembled solely by the CH–π hydrogen bonds. Multivalent interactions of a bowl-shaped hydrocarbon with its peripheral hydrogen atoms are made possible via CH–π hydrogen bonds by adopting a tubular hydrocarbon as a host for their enthalpy-driven complexation. Concyclic arrays of weak hydrogen bonds further allow dynamic rotational motions of the guest in the host. Solid-state analysis with crystallographic and spectroscopic methods reveal a single-axis rotation of the bowl in the tube.

Suggested Citation

  • Taisuke Matsuno & Masahiro Fujita & Kengo Fukunaga & Sota Sato & Hiroyuki Isobe, 2018. "Concyclic CH-π arrays for single-axis rotations of a bowl in a tube," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-06270-6
    DOI: 10.1038/s41467-018-06270-6
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    Cited by:

    1. Toshiya M. Fukunaga & Yuzuka Onaka & Takahide Kato & Koki Ikemoto & Hiroyuki Isobe, 2023. "Stoichiometry validation of supramolecular complexes with a hydrocarbon cage host by van ’t Hoff analyses," Nature Communications, Nature, vol. 14(1), pages 1-8, December.

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