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Linkage control between molecular and supramolecular chirality in 21-helical hydrogen-bonded networks using achiral components

Author

Listed:
  • Toshiyuki Sasaki

    (Graduate School of Engineering, Osaka University)

  • Ichiro Hisaki

    (Graduate School of Engineering, Osaka University)

  • Tetsuya Miyano

    (Graduate School of Engineering, Osaka University)

  • Norimitsu Tohnai

    (Graduate School of Engineering, Osaka University)

  • Kazuya Morimoto

    (Graduate School of Science and Engineering, Ehime University)

  • Hisako Sato

    (Graduate School of Science and Engineering, Ehime University)

  • Seiji Tsuzuki

    (Research Initiative of Computational Sciences (RICS), Nanosystem Research Institute, National Institute of Advanced Industrial Science and Technology (AIST))

  • Mikiji Miyata

    (Graduate School of Engineering, Osaka University)

Abstract

Chiral molecules preferentially form one-handed supramolecular assemblies that reflect the absolute configuration of the molecules. Under specific conditions, however, the opposite-handed supramolecular assemblies are also obtained because of flexibility in the bond length and reversibility of non-covalent interactions. The mechanism of the handedness selectivity or switching phenomenon remains ambiguous, and most phenomena are observed by chance. Here we demonstrate the construction of chiral hydrogen-bonded twofold helical assemblies with controlled handedness in the crystalline state based on crystallographic studies. Detailed investigation of the obtained crystal structures enabled us to clarify the mechanism, and the handedness of the supramolecular chirality was successfully controlled by exploiting achiral factors. This study clearly reveals a connection between molecular chirality and supramolecular chirality in the crystalline state.

Suggested Citation

  • Toshiyuki Sasaki & Ichiro Hisaki & Tetsuya Miyano & Norimitsu Tohnai & Kazuya Morimoto & Hisako Sato & Seiji Tsuzuki & Mikiji Miyata, 2013. "Linkage control between molecular and supramolecular chirality in 21-helical hydrogen-bonded networks using achiral components," Nature Communications, Nature, vol. 4(1), pages 1-7, June.
    • Handle: RePEc:nat:natcom:v:4:y:2013:i:1:d:10.1038_ncomms2756
    DOI: 10.1038/ncomms2756
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