A trefoil knot self-templated through imination in water

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 () and Hao Li ()
Additional contact information
Ye Lei: Zhejiang University
Zhaoyong Li: 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
Feihe Huang: Zhejiang University
Hao Li: Zhejiang University

Nature Communications, 2022, vol. 13, issue 1, 1-7

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-31289-1

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