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Chiral recognition of neutral guests by chiral naphthotubes with a bis-thiourea endo-functionalized cavity

Author

Listed:
  • Song-Meng Wang

    (Southern University of Science and Technology)

  • Yan-Fang Wang

    (Southern University of Science and Technology)

  • Liping Huang

    (Southern University of Science and Technology)

  • Li-Shuo Zheng

    (Southern University of Science and Technology)

  • Hao Nian

    (Southern University of Science and Technology)

  • Yu-Tao Zheng

    (Southern University of Science and Technology)

  • Huan Yao

    (Hengyang Medical School, University of South China)

  • Wei Jiang

    (Southern University of Science and Technology)

  • Xiaoping Wang

    (Southern University of Science and Technology)

  • Liu-Pan Yang

    (Hengyang Medical School, University of South China)

Abstract

Developing chiral receptors with an endo-functionalized cavity for chiral recognition is of great significance in the field of molecular recognition. This study presents two pairs of chiral naphthotubes containing a bis-thiourea endo-functionalized cavity. Each chiral naphthotube has two homochiral centers which were fixed adjacent to the thiourea groups, causing the skeleton and thiourea groups to twist enantiomerically through chiral transfer. These chiral naphthotubes are highly effective at enantiomerically recognizing various neutral chiral molecules with an enantioselectivity up to 17.0. Furthermore, the mechanism of the chiral recognition has been revealed to be originated from differences in multiple non-covalent interactions. Various factors, such as the shape of cavities, substituents of guests, flexibility of host and binding modes are demonstrated to contribute to creating differences in the non-covalent interactions. Additionally, the driving force behind enantioselectivity is mainly attributed to enthalpic differences, and enthalpy -entropy compensation has also been observed to influence enantioselectivity.

Suggested Citation

  • Song-Meng Wang & Yan-Fang Wang & Liping Huang & Li-Shuo Zheng & Hao Nian & Yu-Tao Zheng & Huan Yao & Wei Jiang & Xiaoping Wang & Liu-Pan Yang, 2023. "Chiral recognition of neutral guests by chiral naphthotubes with a bis-thiourea endo-functionalized cavity," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-41390-8
    DOI: 10.1038/s41467-023-41390-8
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