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Precise Control of Radial Catenane Synthesis via Clipping and Pumping

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    Precise Control of Radial Catenane Synthesis via Clipping and Pumping
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    • Anquan Li
      Anquan Li
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Anquan Li
    • Zhengqi Tan
      Zhengqi Tan
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Zhengqi Tan
    • Yiheng Hu
      Yiheng Hu
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Yiheng Hu
    • Zonghuan Lu
      Zonghuan Lu
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Zonghuan Lu
    • Jun Yuan
      Jun Yuan
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Jun Yuan
    • Xia Li
      Xia Li
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Xia Li
    • Jialin Xie
      Jialin Xie
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      More by Jialin Xie
    • Jiangwei Zhang*
      Jiangwei Zhang
      Dalian National Laboratory for Clean Energy & State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China
      *Email: [email protected]
      More by Jiangwei Zhang
      Orcidhttps://orcid.org/0000-0002-1221-3033
    • Kelong Zhu*
      Kelong Zhu
      School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China
      *Email: [email protected]
      More by Kelong Zhu
      Orcidhttps://orcid.org/0000-0002-8339-7298
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 5, 2085–2089
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.1c12303
    Published January 24, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    An unprecedented molecular pumping cassette was designed and implemented for the construction of molecular necklaces, that is, radial [n]catenanes. The mechanism was fully confirmed on a model [2]pseudorotaxane, and the novel clipping-followed-by-pumping strategy was used to prepare a series of [n]catenanes (n = 2–5). A pair of [3]catenane diastereomers sequentially threaded with two different wheels was also accomplished. The success of utilizing molecular pumping to construct molecular necklaces offers new insights into complex molecular architectures and expands the application of molecular machines in synthesis.

    Copyright © 2022 American Chemical Society

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.1c12303.

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    CCDC 1982932 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

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    This article is cited by 35 publications.

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    6. Long Zhang, Huang Wu, Xuesong Li, Hongliang Chen, R. Dean Astumian, J. Fraser Stoddart. Artificial molecular pumps. Nature Reviews Methods Primers 2024, 4 (1) https://doi.org/10.1038/s43586-024-00291-w
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    8. Hanwei Zhang, Jinsa Li, Ziqing Hu, Xiaofan Ji. Poly[2]catenane Gels Based on Sequential Assembly of Small Molecules †. Chinese Journal of Chemistry 2024, 42 (22) , 2699-2704. https://doi.org/10.1002/cjoc.202400435
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 5, 2085–2089
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.1c12303
    Published January 24, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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