Synthesis and properties of fully conjugated macrocycles composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units

Toshiaki Shimasaki, Shunsuke Okajima, Rino Ishikawa, Shinji Kawaguchi, Takeshi Akimoto, Naoto Asano, Tetsuo Iwanaga, Motonori Watanabe, Naozumi Teramoto, Mitsuhiro Shibata

    Research output: Contribution to journalArticlepeer-review

    2 Citations (Scopus)

    Abstract

    Fully conjugated macrocycles 1a−1c composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units were synthesized via Sonogashira cross coupling reactions under high-diluted condition. These conjugated macrocycles were fully characterized by 1H NMR, 13C NMR, FT-IR, Mass spectroscopies and elemental analysis. Photophysical and redox properties of 1a−1c were investigated by means of UV–vis/fluorescence spectroscopies and cyclic voltammetry, respectively, and those features were compared with those of the corresponding linear phenylethynyldibenzoheterols 11a−11c. Furthermore, their structural and electronic insights were studied by theoretical calculations at the B3LYP/cc-pVDZ//B3LYP/6-31G(d) level of theory.

    Original languageEnglish
    Pages (from-to)2454-2465
    Number of pages12
    JournalTetrahedron
    Volume74
    Issue number20
    DOIs
    Publication statusPublished - May 17 2018

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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