A novel redox switch for fluorescence

Drastic UV-vis and fluorescence spectral changes upon electrolysis of a hexaphenylethane derivative of 10,10′-dimethylbiacridan

Takanori Suzuki, Akira Migita, Hiroki Higuchi, Hidetoshi Kawai, Kenshu Fujiwara, Takashi Tsuji

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

The newly prepared title donor 1 has a very long C-C bond [1.635(2) Å], which was readily cleaved upon oxidation to give dication 2 2+ containing two 10-methylacridinium chromophores. Colorless donor 1 (Eox +0.18 V) is non-fluorescent whereas orange dication 2 2+ (Ered -0.27 V) emits strong green fluorescence, so that, this pair can be considered as a novel redox switch for fluorescence with high electrochemical bistability.

Original languageEnglish
Pages (from-to)6837-6840
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number36
DOIs
Publication statusPublished - Sep 1 2003

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Electrolysis
Oxidation-Reduction
Fluorescence
Switches
Derivatives
Chromophores
Oxidation

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A novel redox switch for fluorescence : Drastic UV-vis and fluorescence spectral changes upon electrolysis of a hexaphenylethane derivative of 10,10′-dimethylbiacridan. / Suzuki, Takanori; Migita, Akira; Higuchi, Hiroki; Kawai, Hidetoshi; Fujiwara, Kenshu; Tsuji, Takashi.

In: Tetrahedron Letters, Vol. 44, No. 36, 01.09.2003, p. 6837-6840.

Research output: Contribution to journalArticle

Suzuki, Takanori ; Migita, Akira ; Higuchi, Hiroki ; Kawai, Hidetoshi ; Fujiwara, Kenshu ; Tsuji, Takashi. / A novel redox switch for fluorescence : Drastic UV-vis and fluorescence spectral changes upon electrolysis of a hexaphenylethane derivative of 10,10′-dimethylbiacridan. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 36. pp. 6837-6840.
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