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Hexnut[12]arene and its derivatives: Synthesis, host-guest properties, and application as nonporous adaptive crystals

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Abstract

Hexnut[12]arene (HN[12]) and its derivatives, a new class of sixfold macrocyclic arenes, were designed and synthesized in reasonable yield by a one-pot reaction at room temperature using dimethoxymethane as a methylene source. HN[12], which bears a large, symmetric, and rigid cavity, was easily functionalized at both the methylene bridges and the hydroquinone units. A water-soluble fluorescent HN[12] was synthesized and used as a host to encapsulate benzyl viologen dichloride in water with a high binding affinity of (3.4 ± 0.2) × 106 M−1. The nonporous adaptive crystal (NAC) of HN[12] was found to capture not only inorganic molecules (iodine) but also trace amounts of large organic molecules (basic fuchsine) from water, which greatly expands the scope of NACs for adsorption.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22071066, 21772045), the National Key Research and Development Program of China (2016YFA0602900), the Guangdong Natural Science Foundation, China (2018B030311008, 2018A0303130007, 2019A1515111079, 2021A1515010183), the Guangzhou Science and Technology Project (202002030203, 201902010063), the Postdoctoral Science Foundation of China (2020M672624), the Fundamental Research Funds of the State Key Laboratory of Luminescent Materials and Devices in 2020 (105216000000190044), and the SCUT “Xinghua Scholar Talent Program” (for HT). The authors thank Prof. Yiwei Zhang (SCUT) for fruitful discussion.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510641, China

    Jian Cheng, Bingbing Gao, Hao Tang, Zhihong Sun, Linxian Xu, Lingyun Wang & Derong Cao

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  1. Jian Cheng
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Correspondence to Hao Tang or Derong Cao.

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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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Cheng, J., Gao, B., Tang, H. et al. Hexnut[12]arene and its derivatives: Synthesis, host-guest properties, and application as nonporous adaptive crystals. Sci. China Chem. 65, 539–545 (2022). https://doi.org/10.1007/s11426-021-1186-2

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