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Synthesis, Structures, and Electronic Properties of 2,7-Anthrylene-Based Azacyclophanes Bearing o-, m-, and p-Phenylenediamine Linkers

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    Synthesis, Structures, and Electronic Properties of 2,7-Anthrylene-Based Azacyclophanes Bearing o-, m-, and p-Phenylenediamine Linkers
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    • Tetsuo Iwanaga*
      Tetsuo Iwanaga
      Department of Chemistry, Faculty of Science, Okayama University of Science, 1−1 Ridaicho, Kita-ku, Okayama 700-0005, Japan
      *Email: [email protected]. Phone: +81 86 256 9779. Fax: +81 86 256 9779.
      More by Tetsuo Iwanaga
      Orcidhttps://orcid.org/0000-0002-2224-3746
    • Takashi Komori
      Takashi Komori
      Department of Chemistry, Faculty of Science, Okayama University of Science, 1−1 Ridaicho, Kita-ku, Okayama 700-0005, Japan
      More by Takashi Komori
    • Hiroki Sato
      Hiroki Sato
      Department of Chemistry, Faculty of Science, Okayama University of Science, 1−1 Ridaicho, Kita-ku, Okayama 700-0005, Japan
      More by Hiroki Sato
    • Shuichi Suzuki
      Shuichi Suzuki
      Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560-8531, Japan
      More by Shuichi Suzuki
      Orcidhttps://orcid.org/0000-0001-6294-9084
    • Tomokazu Yamauchi
      Tomokazu Yamauchi
      Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan
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    • Yohji Misaki
      Yohji Misaki
      Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan
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      Orcidhttps://orcid.org/0000-0002-9079-8487
    • Hiroyasu Sato
      Hiroyasu Sato
      X-ray Research Laboratory, Rigaku Corporation, 3−9−12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
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    • Shinji Toyota
      Shinji Toyota
      Department of Chemistry, School of Science, Tokyo Institute of Technology, 2−12−1 Ookayama, Meguro-ku, Tokyo 152−8551, Japan
      More by Shinji Toyota
      Orcidhttps://orcid.org/0000-0002-1504-2030
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2021, 86, 17, 11370–11377
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.1c00856
    Published July 29, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    A series of novel azacyclophanes consisting of 2,7-anthrylene and phenylene units were designed and synthesized by the Buchwald–Hartwig coupling reaction to investigate their unique electronic properties in multiple oxidized states. Cyclic voltammetry showed that the p-phenylene derivative exhibited three reversible oxidation waves, whereas the o- and m-phenylene derivatives showed two quasi-reversible oxidation waves due to the complicated intramolecular interaction between the oxidized units and neutral units. Moreover, the absorption spectra of the p-phenylene derivative in different oxidation states showed absorption bands at 865 and 1025 nm, which were attributed to intramolecular charge–transfer interactions. The photophysical and electrochemical properties of the p-phenylene analog were also compared with those of the o- and m-phenylene derivatives based on theoretical calculations for further evaluation of the intramolecular electronic interactions.

    Copyright © 2021 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/acs.joc.1c00856.

    • 1H and 13C NMR spectra of novel compounds, structural and spectral data, cyclic voltammograms, computational results (PDF)

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    CCDC 1957317–1957319 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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    This article is cited by 4 publications.

    1. Robindo Chatterjee, Bappaditya Goswami, Ambika Devi, Swati Rani, Manas Khatua, Subhas Samanta. Completely o-Phenylene Bridged N4-Cyclophane: A Missing Link in the Phenylene Bridge N4-Cyclophane Family. Organic Letters 2023, 25 (21) , 3946-3950. https://doi.org/10.1021/acs.orglett.3c01326
    2. Tetsuo Iwanaga, Tomohiro Oki, Yoshihiro Morioka, Shoichiro Inoue, Hiroyasu Sato. Synthesis of π-Extended Carbazole Dimers Via Oxidative Cyclization Using DDQ and Sulfonic Acid and Elucidation of the Reaction Mechanism. The Journal of Organic Chemistry 2022, 87 (21) , 14855-14860. https://doi.org/10.1021/acs.joc.2c01571
    3. Charles N. Moorefield, George R. Newkome. Eight-membered and larger rings. 2023, 609-626. https://doi.org/10.1016/B978-0-443-18939-5.00017-2
    4. Taichi Kurimoto, Yusuke Inagaki, Kazuaki Ohara, Kentaro Yamaguchi, Wataru Setaka. Synthesis and rotational dynamics of diazamacrocycles having bridged 1,4-naphthylene as framed molecular rotors. Organic & Biomolecular Chemistry 2022, 20 (43) , 8465-8470. https://doi.org/10.1039/D2OB01613C
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2021, 86, 17, 11370–11377
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.1c00856
    Published July 29, 2021
    Copyright © 2021 American Chemical Society
    Request reuse permissions

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