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

doi:10.1016/j.tet.2018.03.072

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

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5 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 language	English
Pages (from-to)	2454-2465
Number of pages	12
Journal	Tetrahedron
Volume	74
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2018.03.072
Publication status	Published - May 17 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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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, 74(20), 2454-2465. https://doi.org/10.1016/j.tet.2018.03.072

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

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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.",

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

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AU - Shimasaki, Toshiaki

AU - Okajima, Shunsuke

AU - Ishikawa, Rino

AU - Kawaguchi, Shinji

AU - Akimoto, Takeshi

AU - Asano, Naoto

AU - Iwanaga, Tetsuo

AU - Watanabe, Motonori

AU - Teramoto, Naozumi

AU - Shibata, Mitsuhiro

PY - 2018/5/17

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N2 - 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.

AB - 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.

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

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