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A trefoil knot self-templated through imination in water

Author

Listed:
  • Ye Lei

    (Zhejiang University)

  • Zhaoyong Li

    (Zhejiang University
    Zhejiang University)

  • Guangcheng Wu

    (Zhejiang University)

  • Lijie Zhang

    (Zhejiang Normal University)

  • Lu Tong

    (Zhejiang University)

  • Tianyi Tong

    (Xiamen University)

  • Qiong Chen

    (Zhejiang University)

  • Lingxiang Wang

    (Zhejiang University)

  • Chenqi Ge

    (Zhejiang University)

  • Yuxi Wei

    (Zhejiang University)

  • Yuanjiang Pan

    (Zhejiang University)

  • Andrew C.-H. Sue

    (Xiamen University)

  • Linjun Wang

    (Zhejiang University
    Zhejiang University)

  • Feihe Huang

    (Zhejiang University
    ZJU-Hangzhou Global Scientific and Technological Innovation Center)

  • Hao Li

    (Zhejiang University
    ZJU-Hangzhou Global Scientific and Technological Innovation Center)

Abstract

The preparation of topologically nontrivial molecules is often assisted by covalent, supramolecular or coordinative templates that provide spatial pre-organization for all components. Herein, we report a trefoil knot that can be self-assembled efficiently in water without involving additional templates. The direct condensation of three equivalents of a tetraformyl precursor and six equivalents of a chiral diamine produces successfully a [3 + 6] trefoil knot whose intrinsic handedness is dictated by the stereochemical configuration of the diamine linkers. Contrary to the conventional wisdom that imine condensation is not amenable to use in water, the multivalent cooperativity between all the imine bonds within the framework makes this trefoil knot robust in the aqueous environment. Furthermore, the presence of water is proven to be essential for the trefoil knot formation. A topologically trivial macrocycle composed of two tetraformyl and four diamino building blocks is obtained when a similar reaction is performed in organic media, indicating that hydrophobic effect is a major driving force behind the scene.

Suggested Citation

  • Ye Lei & Zhaoyong Li & Guangcheng Wu & Lijie Zhang & Lu Tong & Tianyi Tong & Qiong Chen & Lingxiang Wang & Chenqi Ge & Yuxi Wei & Yuanjiang Pan & Andrew C.-H. Sue & Linjun Wang & Feihe Huang & Hao Li, 2022. "A trefoil knot self-templated through imination in water," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31289-1
    DOI: 10.1038/s41467-022-31289-1
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    References listed on IDEAS

    as
    1. Ankit Jain & Shikha Dhiman & Ashish Dhayani & Praveen K. Vemula & Subi J. George, 2019. "Chemical fuel-driven living and transient supramolecular polymerization," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    2. William R. Taylor, 2000. "A deeply knotted protein structure and how it might fold," Nature, Nature, vol. 406(6798), pages 916-919, August.
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