4,7-Bis(dimethylamino)benzimidazoles and twin-type derivatives: Reversible two-stage redox system modulated by- proton-transfer

Takanori Suzuki; Yoshiaki Tsubata; Yoshiaki Obana; Takanori Fukushima; Tsutomu Miyashi; Mayu Saito; Hidetoshi Kawai; Kenshu Fujiwara; Kimio Akiyama

doi:10.1016/j.tetlet.2003.09.012

4,7-Bis(dimethylamino)benzimidazoles and twin-type derivatives: Reversible two-stage redox system modulated by- proton-transfer

Takanori Suzuki, Yoshiaki Tsubata, Yoshiaki Obana, Takanori Fukushima, Tsutomu Miyashi, Mayu Saito, Hidetoshi Kawai, Kenshu Fujiwara, Kimio Akiyama

Division of Organic- and Biomaterials Research

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

4 Citations (Scopus)

Abstract

The title electron donors 1 as well as their conjugate bases 2^- undergo reversible two-stage one-electron oxidation. ESR analysis indicated the important contribution of zwitterionic structure for radicals 2·. Bis(zwitterionic) but not quinoid structure was suggested for p-4, generated from the twin-type dianionic donor p-4^2- with a p-phenylene spacer.

Original language	English
Pages (from-to)	7881-7884
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2003.09.012
Publication status	Published - 2003 Oct 20

Keywords

Electrochromism
Electron donor
Phenylenediamine
Proton transfer
Radical
Redox system
Response system
Zwitterion

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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4,7-Bis(dimethylamino)benzimidazoles and twin-type derivatives : Reversible two-stage redox system modulated by- proton-transfer. / Suzuki, Takanori; Tsubata, Yoshiaki; Obana, Yoshiaki; Fukushima, Takanori; Miyashi, Tsutomu; Saito, Mayu; Kawai, Hidetoshi; Fujiwara, Kenshu; Akiyama, Kimio.

In: Tetrahedron Letters, Vol. 44, No. 43, 20.10.2003, p. 7881-7884.

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

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title = "4,7-Bis(dimethylamino)benzimidazoles and twin-type derivatives: Reversible two-stage redox system modulated by- proton-transfer",

abstract = "The title electron donors 1 as well as their conjugate bases 2- undergo reversible two-stage one-electron oxidation. ESR analysis indicated the important contribution of zwitterionic structure for radicals 2·. Bis(zwitterionic) but not quinoid structure was suggested for p-4, generated from the twin-type dianionic donor p-42- with a p-phenylene spacer.",

keywords = "Electrochromism, Electron donor, Phenylenediamine, Proton transfer, Radical, Redox system, Response system, Zwitterion",

author = "Takanori Suzuki and Yoshiaki Tsubata and Yoshiaki Obana and Takanori Fukushima and Tsutomu Miyashi and Mayu Saito and Hidetoshi Kawai and Kenshu Fujiwara and Kimio Akiyama",

note = "Funding Information: This work was supported by the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 15350019 and 14654139). We thank Professor Tamotsu Inabe (Hokkaido University) for use of the X-ray structure analysis system.",

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T2 - Reversible two-stage redox system modulated by- proton-transfer

AU - Suzuki, Takanori

AU - Tsubata, Yoshiaki

AU - Obana, Yoshiaki

AU - Fukushima, Takanori

AU - Miyashi, Tsutomu

AU - Saito, Mayu

AU - Kawai, Hidetoshi

AU - Fujiwara, Kenshu

AU - Akiyama, Kimio

N1 - Funding Information: This work was supported by the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 15350019 and 14654139). We thank Professor Tamotsu Inabe (Hokkaido University) for use of the X-ray structure analysis system.

PY - 2003/10/20

Y1 - 2003/10/20

N2 - The title electron donors 1 as well as their conjugate bases 2- undergo reversible two-stage one-electron oxidation. ESR analysis indicated the important contribution of zwitterionic structure for radicals 2·. Bis(zwitterionic) but not quinoid structure was suggested for p-4, generated from the twin-type dianionic donor p-42- with a p-phenylene spacer.

AB - The title electron donors 1 as well as their conjugate bases 2- undergo reversible two-stage one-electron oxidation. ESR analysis indicated the important contribution of zwitterionic structure for radicals 2·. Bis(zwitterionic) but not quinoid structure was suggested for p-4, generated from the twin-type dianionic donor p-42- with a p-phenylene spacer.

KW - Electrochromism

KW - Electron donor

KW - Phenylenediamine

KW - Proton transfer

KW - Radical

KW - Redox system

KW - Response system

KW - Zwitterion

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EP - 7884

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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IS - 43

ER -

4,7-Bis(dimethylamino)benzimidazoles and twin-type derivatives: Reversible two-stage redox system modulated by- proton-transfer

Abstract

Keywords

ASJC Scopus subject areas

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