Synthesis and Properties of Cyclic π-Conjugated Molecules and Their Dication and Monoradical Cation

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  • Xu, Runjie
    Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Kuninobu, Yoichiro
    Institute for Materials Chemistry and Engineering, Kyushu University Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

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Description

We synthesized cyclic π-conjugated molecules by double Friedel–Crafts reaction of amino group-substituted 1,2-bis(2-phenylethynyl)benzene with Meldrum’s acid derivative. The structures of the cyclic π-conjugated molecules were determined by single-crystal X-ray structure analysis. The oxidation of the dimethylamino group-substituted π-conjugated molecule with NOBF_4 gave a closed-shell dication that is stable at >210 °C. The monoradical cation of the di(4-methoxyphenyl)amino group-substituted π-conjugated molecule is stable in dichloromethane solution (half-life of nearly 15 days) and shows near-infrared absorption.

Journal

  • Organic Letters

    Organic Letters 26 (26), 5582-5586, 2024-06-20

    American Chemical Society (ACS)

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