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Corralarenes: A Family of Conjugated Tubular Hosts
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    Corralarenes: A Family of Conjugated Tubular Hosts
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    • Han Han
      Han Han
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
      More by Han Han
    • Rong Fu
      Rong Fu
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
      More by Rong Fu
    • Ruiguo Wang
      Ruiguo Wang
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
      More by Ruiguo Wang
    • Chun Tang
      Chun Tang
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
      More by Chun Tang
    • Miao-Miao He
      Miao-Miao He
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
      More by Miao-Miao He
    • Jia-Ying Deng
      Jia-Ying Deng
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
    • Dong-Sheng Guo
      Dong-Sheng Guo
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
    • J. Fraser Stoddart
      J. Fraser Stoddart
      Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States
      Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310027, China
      ZJU-Hangzhou Global Scientific and Technological Innovation Center, Hangzhou 311215, China
      School of Chemistry, University of New South Wales, Sydney 2052, NSW, Australia
    • Kang Cai*
      Kang Cai
      College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300072, China
      *Email: [email protected]
      More by Kang Cai
    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 44, 20351–20362
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    https://doi.org/10.1021/jacs.2c08144
    Published October 20, 2022
    Copyright © 2022 American Chemical Society

    Abstract

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    Despite the advances in host–guest chemistry, macrocyclic hosts with deep cavities are far from abundant among the large number of wholly synthetic hosts described in the literature. Herein, we describe the design and synthesis of two new tubular hosts, namely, corral[4]arene and corral[5]arene. The former has been isolated and characterized as two conformational diastereoisomers, one is centrosymmetric and the other asymmetric. The latter, a fivefold symmetrical and flexible host, has also been investigated in detail. It is composed of five 4,4′-dimethoxybiphenyl units bridged by ethynylene linkers at their 2,2′-positions and adopts a pentagonal conformation with a tubular-shaped cavity in the presence of guests. This structure endows corral[5]arene not only with a conjugated backbone, capable of bright fluorescent emission (quantum yield, 56%), but also a deep π-electron-rich aromatic cavity with remarkable conformational flexibility. The adaptive cavity of corral[5]arene allows it to accommodate a wide range of neutral and positively charged electron-deficient guests with different molecular sizes and shapes. Binding constants between this host and these guests in three different nonpolar organic solvents lie in the range of 103 to 107 M–1. Moreover, corral[5]arene exhibits dynamic chirality on account of the axes of chirality associated with each of the five biphenyl units and displays first-order transformation as exhibited by circular dichroism in response to the addition of chiral guests. All these stereochemical features render corral[5]arene an attractive host for a variety of supramolecular and nanotechnological applications.

    Copyright © 2022 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c08144.

    • Detailed experimental sections, structural characterization data, host–guest characterizations, and theoretical calculations (PDF)

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    CCDC 21713382171339, 21713412171342, 2171884, 2192791, and 2192793 contain 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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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2022, 144, 44, 20351–20362
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.2c08144
    Published October 20, 2022
    Copyright © 2022 American Chemical Society

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