Fluorescence properties of 3- and 4-trifluoroacetylamino-1,8- naphthalimides: Solvent-controlled switching of fluorescence color and response to metal-cations

Hideki Okamoto, Kyosuke Satake, Masaru Kimura

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The effects of solvents and metal cations on the fluorescence spectra of 3- (1) and 4- (2) trifluoroacetylamino-1,8-naphthalimides were investigated. In MeCN, these naphthalimides displayed a violet ∼ blue fluorescence based on their neutral amide form (1, 2). Whereas in DMSO, they gave off a yellow ∼ orange emission due to their amide anions (1-, 2-). In MeOH, naphthalimide 2 emitted a dual fluorescence (λFL 436 and 556 nm) to display a white luminescence. Naphthalimides 1, 2 are essentially insensitive to metal cations in their neutral amide form. In contrast, the fluorescence of the amide anions 1-, 2- was quenched by metal cations. The efficiency of the quenching correlated with the Lewis acidity of the metal cations; a stronger Lewis acid tended to display a more effective fluorescence quenching. Therefore, the fluorescence color and the sensitivity to metal cations of the naphthalimides were effectively switched by the solvent.

Original languageEnglish
Pages (from-to)112-123
Number of pages12
JournalArkivoc
Volume2007
Issue number8
Publication statusPublished - 2007

Fingerprint

Naphthalimides
Cations
Metals
Fluorescence
Color
Amides
Anions
Quenching
Lewis Acids
Dimethyl Sulfoxide
Acidity
Luminescence

Keywords

  • 1,8-naphthalimide
  • Fluorescence
  • Metal cation
  • Solvent effects
  • Switching
  • White fluorescence

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Fluorescence properties of 3- and 4-trifluoroacetylamino-1,8- naphthalimides : Solvent-controlled switching of fluorescence color and response to metal-cations. / Okamoto, Hideki; Satake, Kyosuke; Kimura, Masaru.

In: Arkivoc, Vol. 2007, No. 8, 2007, p. 112-123.

Research output: Contribution to journalArticle

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N2 - The effects of solvents and metal cations on the fluorescence spectra of 3- (1) and 4- (2) trifluoroacetylamino-1,8-naphthalimides were investigated. In MeCN, these naphthalimides displayed a violet ∼ blue fluorescence based on their neutral amide form (1, 2). Whereas in DMSO, they gave off a yellow ∼ orange emission due to their amide anions (1-, 2-). In MeOH, naphthalimide 2 emitted a dual fluorescence (λFL 436 and 556 nm) to display a white luminescence. Naphthalimides 1, 2 are essentially insensitive to metal cations in their neutral amide form. In contrast, the fluorescence of the amide anions 1-, 2- was quenched by metal cations. The efficiency of the quenching correlated with the Lewis acidity of the metal cations; a stronger Lewis acid tended to display a more effective fluorescence quenching. Therefore, the fluorescence color and the sensitivity to metal cations of the naphthalimides were effectively switched by the solvent.

AB - The effects of solvents and metal cations on the fluorescence spectra of 3- (1) and 4- (2) trifluoroacetylamino-1,8-naphthalimides were investigated. In MeCN, these naphthalimides displayed a violet ∼ blue fluorescence based on their neutral amide form (1, 2). Whereas in DMSO, they gave off a yellow ∼ orange emission due to their amide anions (1-, 2-). In MeOH, naphthalimide 2 emitted a dual fluorescence (λFL 436 and 556 nm) to display a white luminescence. Naphthalimides 1, 2 are essentially insensitive to metal cations in their neutral amide form. In contrast, the fluorescence of the amide anions 1-, 2- was quenched by metal cations. The efficiency of the quenching correlated with the Lewis acidity of the metal cations; a stronger Lewis acid tended to display a more effective fluorescence quenching. Therefore, the fluorescence color and the sensitivity to metal cations of the naphthalimides were effectively switched by the solvent.

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