Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon: Preparation, X-ray structures, and electrochromic response with fluorescence change

Takanori Suzuki; Shoko Tanaka; Hiroki Higuchi; Hidetoshi Kawai; Kenshu Fujiwara

doi:10.1016/j.tetlet.2004.09.080

Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon: Preparation, X-ray structures, and electrochromic response with fluorescence change

Takanori Suzuki, Shoko Tanaka, Hiroki Higuchi, Hidetoshi Kawai, Kenshu Fujiwara

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

The long C-C bonds (1.614(2)-1.630(2) Å) in newly prepared title donors 2-6 are cleaved upon two-electron oxidation to afford the bond-dissociated dicationic dyes 2 ²⁺-6 ²⁺, whose electron affinities are stronger than the corresponding biphenyl-2,2′-diyl dications 1 ²⁺ due to the spatial proximity of two xanthenylium units. Not only UV-vis but also fluorescence spectra changed drastically upon electrolysis since only colorless neutral donors are fluorescent.

Original language	English
Pages (from-to)	8563-8567
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2004.09.080
Publication status	Published - Nov 8 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.09.080

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Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon : Preparation, X-ray structures, and electrochromic response with fluorescence change. / Suzuki, Takanori; Tanaka, Shoko; Higuchi, Hiroki et al.

In: Tetrahedron Letters, Vol. 45, No. 46, 08.11.2004, p. 8563-8567.

Research output: Contribution to journal › Article › peer-review

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title = "Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon: Preparation, X-ray structures, and electrochromic response with fluorescence change",

abstract = "The long C-C bonds (1.614(2)-1.630(2) {\AA}) in newly prepared title donors 2-6 are cleaved upon two-electron oxidation to afford the bond-dissociated dicationic dyes 2 2+-6 2+, whose electron affinities are stronger than the corresponding biphenyl-2,2′-diyl dications 1 2+ due to the spatial proximity of two xanthenylium units. Not only UV-vis but also fluorescence spectra changed drastically upon electrolysis since only colorless neutral donors are fluorescent.",

author = "Takanori Suzuki and Shoko Tanaka and Hiroki Higuchi and Hidetoshi Kawai and Kenshu Fujiwara",

note = "Funding Information: This work was supported by the Ministry of Education, Science, and Culture, Japan (No. 15350019 and 14654139). We thank Prof. Tamotsu Inabe (Hokkaido University) for use of the X-ray structure analysis system. MS spectra were measured by Mr. Kenji Watanabe and Dr. Eri Fukushi at the GC–MS, and NMR Laboratory (Faculty of Agriculture, Hokkaido University). ",

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AU - Suzuki, Takanori

AU - Tanaka, Shoko

AU - Higuchi, Hiroki

AU - Kawai, Hidetoshi

AU - Fujiwara, Kenshu

N1 - Funding Information: This work was supported by the Ministry of Education, Science, and Culture, Japan (No. 15350019 and 14654139). We thank Prof. Tamotsu Inabe (Hokkaido University) for use of the X-ray structure analysis system. MS spectra were measured by Mr. Kenji Watanabe and Dr. Eri Fukushi at the GC–MS, and NMR Laboratory (Faculty of Agriculture, Hokkaido University).

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AB - The long C-C bonds (1.614(2)-1.630(2) Å) in newly prepared title donors 2-6 are cleaved upon two-electron oxidation to afford the bond-dissociated dicationic dyes 2 2+-6 2+, whose electron affinities are stronger than the corresponding biphenyl-2,2′-diyl dications 1 2+ due to the spatial proximity of two xanthenylium units. Not only UV-vis but also fluorescence spectra changed drastically upon electrolysis since only colorless neutral donors are fluorescent.

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Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon: Preparation, X-ray structures, and electrochromic response with fluorescence change

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