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Lemniscular [16]Cycloparaphenylene: A Radially Conjugated Figure-Eight Aromatic Molecule

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    Lemniscular [16]Cycloparaphenylene: A Radially Conjugated Figure-Eight Aromatic Molecule
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    • Kabali Senthilkumar
      Kabali Senthilkumar
      Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
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      Orcidhttp://orcid.org/0000-0002-9409-716X
    • Mateusz Kondratowicz
      Mateusz Kondratowicz
      Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
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    • Tadeusz Lis
      Tadeusz Lis
      Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
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    • Piotr J. Chmielewski
      Piotr J. Chmielewski
      Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
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    • Joanna Cybińska
      Joanna Cybińska
      Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
      PORT − Polski Ośrodek Rozwoju Technologii, ul. Stabłowicka 147, 54-066 Wrocław, Poland
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    • José L. Zafra
      José L. Zafra
      Departamento Química Física, Universidad de Málaga, Andalucia-Tech Campus de Teatinos s/n, 29071 Málaga, Spain
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    • Juan Casado*
      Juan Casado
      Departamento Química Física, Universidad de Málaga, Andalucia-Tech Campus de Teatinos s/n, 29071 Málaga, Spain
      *[email protected]
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      Orcidhttp://orcid.org/0000-0003-0373-1303
    • Thomas Vives
      Thomas Vives
      Université Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France
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    • Jeanne Crassous
      Jeanne Crassous
      Université Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, F-35000 Rennes, France
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      Orcidhttp://orcid.org/0000-0002-4037-6067
    • Ludovic Favereau
      Ludovic Favereau
      Université Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, F-35000 Rennes, France
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    • Marcin Stępień*
      Marcin Stępień
      Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
      *[email protected]
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      Orcidhttp://orcid.org/0000-0002-4670-8093
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2019, 141, 18, 7421–7427
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    https://doi.org/10.1021/jacs.9b01797
    Published April 18, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    A cycloparaphenylene-based molecular lemniscate (CPPL) was obtained in a short synthesis involving masked p-phenylene equivalents. The strained figure-eight geometry of CPPL is sustained by the incorporated 9,9′-bicarbazole subunit, which also acts as a stereogenic element. The shape of the distorted [16]cycloparaphenylene nanohoop embedded in CPPL is accurately approximated with a Booth lemniscate. The structure of CPPL, investigated using NMR and Raman spectroscopic methods, revealed strain-dependent features, consistent with the variable curvature of the ring. The electronic and optical properties of CPPL combine features more characteristic of smaller cycloparaphenylenes, such as a reduced optical bandgap and red-shifted fluorescence. CPPL was resolved into enantiomers, which are configurationally stable and provide strong chiroptical responses, including circularly polarized luminescence.

    Copyright © 2019 American Chemical Society

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    Cite this: J. Am. Chem. Soc. 2019, 141, 18, 7421–7427
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