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 journalArticle

36 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 languageEnglish
Pages (from-to)8563-8567
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number46
DOIs
Publication statusPublished - Nov 8 2004

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Electron affinity
Polycyclic Aromatic Hydrocarbons
Electrolysis
Oxidation-Reduction
Fluorescence
X-Rays
Electrons
X rays
Oxidation
2-(2-(2-chloro-3-(2-(3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl)-vinyl)-cyclohex-2-enylidene)-ethylidene)-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid
diphenyl

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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; Kawai, Hidetoshi; Fujiwara, Kenshu.

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

Research output: Contribution to journalArticle

Suzuki, Takanori ; Tanaka, Shoko ; Higuchi, Hiroki ; Kawai, Hidetoshi ; Fujiwara, Kenshu. / Dynamic redox systems based on bis(spiroxanthene)-type donors with a polycyclic aromatic hydrocarbon : Preparation, X-ray structures, and electrochromic response with fluorescence change. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 46. pp. 8563-8567.
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