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Convenient Syntheses and Photophysical Properties of 1-Thio- and 1-Seleno-1,3-Butadiene Fluorophores in Rigid Dibenzobarrelene and Benzobarrelene Skeletons

Authors

  • Prof. Dr. Akihiko Ishii,

    Corresponding author
    1. Department of Chemistry, Faculty of Science and Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 (Japan), Fax: (+81) 48-858-3394
    • Department of Chemistry, Faculty of Science and Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 (Japan), Fax: (+81) 48-858-3394
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  • Tatsuro Annaka,

    1. Department of Chemistry, Faculty of Science and Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 (Japan), Fax: (+81) 48-858-3394
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  • Dr. Norio Nakata

    1. Department of Chemistry, Faculty of Science and Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 (Japan), Fax: (+81) 48-858-3394
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Abstract

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No heavy-atom effect: Highly fluorescent, sulfur- or selenium-containing compounds were synthesized by intramolecular [4+2]-cycloadditions between 9-anthryl or 1-naphthyl and alkynyl moieties (see scheme). Their fluorescence is based on a 1-chalcogeno-1,3-butadiene-conjugated system in a rigid skeleton. Some of them are also highly fluorescent in the solid state. The monoxide of Mbb-S is more fluorescent in the solid state (ΦF=0.6) than in solution (ΦF<0.02).

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