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Cucurbit[n]urils (n = 7, 8) can strongly bind neutral hydrophilic molecules in water

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Abstract

It is challenging to recognize neutral hydrophilic molecules in water. Effective use of hydrogen bonds in water is generally accepted to be the key to success. In contrast, hydrophobic cavity is usually considered to play an insignificant role or only to provide a nonpolar microenvironment for hydrogen bonds. Herein, we report that hydrophobic cavity alone can also strongly bind neutral, highly hydrophilic molecules in water. We found that cucurbit[n]urils (n = 7, 8) bind 1,4-dioxane, crown ethers and monosaccharides in water with remarkable affinities. The best binding constant reaches 107 M−1 for cucurbit[8]uril, which is higher than its binding affinities to common organic cations. Density functional theory (DFT) calculations and control experiments reveal that the hydrophobic effect is the major contributor to the binding through releasing the cavity water and/or properly occupying the weakly hydrated cavity. However, hydrophobic cavity still prefers nonpolar guests over polar guests with similar size and shape.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22101125), Shenzhen Science and Technology Innovation Committee (JCYJ20180504165810828), Shenzhen “Pengcheng Scholar”, Guangdong High-Level Personnel of Special Support Program (2019TX05C157), and Guangdong Provincial Key Laboratory of Catalysis (2020B121201002). We are grateful to the technical support from SUSTech-CRF and the Center for Computational Science and Engineering of SUSTech.

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  1. School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, 150001, China

    Ming-Shuang Li

  2. Shenzhen Grubbs Institute, Guangdong Provincial Key Laboratory of Catalysis, Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, China

    Ming-Shuang Li, Mao Quan, Xi-Ran Yang & Wei Jiang

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  1. Ming-Shuang Li
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  2. Mao Quan
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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors

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Li, MS., Quan, M., Yang, XR. et al. Cucurbit[n]urils (n = 7, 8) can strongly bind neutral hydrophilic molecules in water. Sci. China Chem. 65, 1733–1740 (2022). https://doi.org/10.1007/s11426-022-1312-5

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