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 journalArticle

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

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Fluorescence Spectrometry
Cross Reactions
Oxidation-Reduction
Mass Spectrometry
Nuclear magnetic resonance
Fluorescence spectroscopy
Cyclic voltammetry
Spectroscopy
Chemical analysis
dibenzofuran
Proton Magnetic Resonance Spectroscopy
dibenzothiophene
carbazole
Carbon-13 Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis and properties of fully conjugated macrocycles composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units. / Shimasaki, Toshiaki; Okajima, Shunsuke; Ishikawa, Rino; Kawaguchi, Shinji; Akimoto, Takeshi; Asano, Naoto; Iwanaga, Tetsuo; Watanabe, Motonori; Teramoto, Naozumi; Shibata, Mitsuhiro.

In: Tetrahedron, Vol. 74, No. 20, 17.05.2018, p. 2454-2465.

Research output: Contribution to journalArticle

Shimasaki, T, Okajima, S, Ishikawa, R, Kawaguchi, S, Akimoto, T, Asano, N, Iwanaga, T, Watanabe, M, Teramoto, N & Shibata, M 2018, 'Synthesis and properties of fully conjugated macrocycles composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units', Tetrahedron, vol. 74, no. 20, pp. 2454-2465. https://doi.org/10.1016/j.tet.2018.03.072
Shimasaki, Toshiaki ; Okajima, Shunsuke ; Ishikawa, Rino ; Kawaguchi, Shinji ; Akimoto, Takeshi ; Asano, Naoto ; Iwanaga, Tetsuo ; Watanabe, Motonori ; Teramoto, Naozumi ; Shibata, Mitsuhiro. / Synthesis and properties of fully conjugated macrocycles composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units. In: Tetrahedron. 2018 ; Vol. 74, No. 20. pp. 2454-2465.
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