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Real-time chirality transfer monitoring from statistically random to discrete homochiral nanotubes

Author

Listed:
  • Shixin Fa

    (Kyoto University
    Northwestern Polytechnical University)

  • Tan-hao Shi

    (Kyoto University)

  • Suzu Akama

    (Kyoto University)

  • Keisuke Adachi

    (Kyoto University)

  • Keisuke Wada

    (Kyoto University)

  • Seigo Tanaka

    (Kyoto University)

  • Naoki Oyama

    (Kyoto University)

  • Kenichi Kato

    (Kyoto University)

  • Shunsuke Ohtani

    (Kyoto University)

  • Yuuya Nagata

    (Hokkaido University)

  • Shigehisa Akine

    (Kanazawa University
    Kanazawa University)

  • Tomoki Ogoshi

    (Kyoto University
    Kanazawa University)

Abstract

Real time monitoring of chirality transfer processes is necessary to better understand their kinetic properties. Herein, we monitor an ideal chirality transfer process from a statistically random distribution to a diastereomerically pure assembly in real time. The chirality transfer is based on discrete trimeric tubular assemblies of planar chiral pillar[5]arenes, achieving the construction of diastereomerically pure trimers of pillar[5]arenes through synergistic effect of ion pairing between a racemic rim-differentiated pillar[5]arene pentaacid bearing five benzoic acids on one rim and five alkyl chains on the other, and an optically resolved pillar[5]arene decaamine bearing ten amines. When the decaamine is mixed with the pentaacid, the decaamine is sandwiched by two pentaacids through ten ion pairs, initially producing a statistically random mixture of a homochiral trimer and two heterochiral trimers. The heterochiral trimers gradually dissociate and reassemble into the homochiral trimers after unit flipping of the pentaacid, leading to chirality transfer from the decaamine and producing diastereomerically pure trimers.

Suggested Citation

  • Shixin Fa & Tan-hao Shi & Suzu Akama & Keisuke Adachi & Keisuke Wada & Seigo Tanaka & Naoki Oyama & Kenichi Kato & Shunsuke Ohtani & Yuuya Nagata & Shigehisa Akine & Tomoki Ogoshi, 2022. "Real-time chirality transfer monitoring from statistically random to discrete homochiral nanotubes," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34827-z
    DOI: 10.1038/s41467-022-34827-z
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    References listed on IDEAS

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    1. Peter A. Korevaar & Subi J. George & Albert J. Markvoort & Maarten M. J. Smulders & Peter A. J. Hilbers & Albert P. H. J. Schenning & Tom F. A. De Greef & E. W. Meijer, 2012. "Pathway complexity in supramolecular polymerization," Nature, Nature, vol. 481(7382), pages 492-496, January.
    2. Nathan J. Van Zee & Beatrice Adelizzi & Mathijs F. J. Mabesoone & Xiao Meng & Antonio Aloi & R. Helen Zha & Martin Lutz & Ivo A. W. Filot & Anja R. A. Palmans & E. W. Meijer, 2018. "Potential enthalpic energy of water in oils exploited to control supramolecular structure," Nature, Nature, vol. 558(7708), pages 100-103, June.
    3. Xinchang Wang & Yu Wang & Huayan Yang & Hongxun Fang & Ruixue Chen & Yibin Sun & Nanfeng Zheng & Kai Tan & Xin Lu & Zhongqun Tian & Xiaoyu Cao, 2016. "Assembled molecular face-rotating polyhedra to transfer chirality from two to three dimensions," Nature Communications, Nature, vol. 7(1), pages 1-7, November.
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