Letter | Published:

Homochiral porous nanosheets for enantiomer sieving

Nature Materials (2018) | Download Citation

Abstract

Protein pores are highly specific in binding to chiral substrates and in catalysing stereospecific reactions, because their active pockets are asymmetric and stereoselective1,2. Chiral binding materials from molecular-level pores with high specificity have not been achieved because of problems with pore deformation and blocking3. A promising solution is the self-assembly of single sheets where all pores are exposed to the environment, for example as metal–organic frameworks4, polymers5,6 or non-covalent aromatic networks7,8,9,10, but, typically, the pores are distant from the internal cavities with chirality. Here, we report the synthesis of homochiral porous nanosheets achieved by the 2D self-assembly of non-chiral macrocycles, with open/closed pore switching. Pore chirality is spontaneously induced by a twisted stack of dimeric macrocycles. The porous 2D structures can serve as enantiomer sieving membranes that exclusively capture a single enantiomer in a racemic mixture solution, with uptake capacity greater than 96%. Moreover, the entrapped guests inside the pores can be pumped out by pore closing triggered by external stimuli. This strategy could provide new opportunities for controlled molecule release, as well as for artificial cells.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (grants 21634005, 51473062 and 21574055) and Jilin University Funding (JLUSTIRT).

Author information

Affiliations

  1. State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, China

    • Bo Sun
    • , Yongju Kim
    • , Yanqiu Wang
    • , Huaxin Wang
    • , Xin Liu
    •  & Myongsoo Lee
  2. Pohang Accelerator Laboratory, Postech, Pohang, Gyeongbuk, Korea

    • Jehan Kim

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Contributions

B.S. synthesized molecules, measured spectroscopic data, carried out the uptake experiments. Y.K. performed chiral separation and molecular simulations, and supervised the research. Y.W. performed TEM experiments. H.W. carried out NMR experiments. J.K. performed X-ray experiments. X.L. measured electron diffraction. M.L. developed the concept, supervised the research and wrote the manuscript with input from all authors.

Competing interests

The authors declare no competing interests.

Corresponding authors

Correspondence to Yongju Kim or Myongsoo Lee.

Electronic supplementary material

  1. Supplementary information

    Supplementary Schemes 1–2, Supplementary Figures 1–34, Supplementary References 1–3

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DOI

https://doi.org/10.1038/s41563-018-0107-4

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