Excited-state and ground-state proton-transfer reactions in 5-aminoindole.

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概要

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• Dual fluorescence emissions are observed when the electron-donating group (–NH<SUB>2</SUB>) is present at the position 5 of indole moiety. From the study of solvent effect and the large blue shift observed in the fluorescence spectra at 77 K, it is concluded that the long wavelength fluorescence band (480 nm) is assigned to the more polar state and the short wavelength band (350 nm) to the less polar state of 5-aminoindole (AI). Monocation is formed by protonating the amino group and no proton-induced fluorescence quenching of the neutral species is observed prior to its being protonated. This is mainly due to the shorter life of the conjugated acid–base pair. CNDO/S calculations indicate that dication is formed by protonating the C-3 position of the monocation of AI in the S<SUB>0</SUB> state but position 4 of monocation of AI in the S<SUB>1</SUB> state. Monoanion is formed by the deprotonation of >NH group in the S<SUB>0</SUB> state, but from the deprotonation of –NH<SUB>2</SUB> group in the S<SUB>1</SUB> state.

• 公益社団法人 日本化学会の論文

著者

• Dogra Sneh

  Department Of Chemistry I. I. T.

• Krishnamurthy Mannam

  Department of Chemistry, A.U.P.G. Extension Centre

• Sinha Hemant

  Department of Chemistry, Indian Institute of Technology

関連論文

• Excited State Intramolecular Proton Transfer Reactions in 2-(2-Hydroxyphenyl)benzimidazole in Micellar Solutions
• Solvatochromism and Prototropism in 2-(Aminophenyl)benzothiazoles.
• Electronic spectra of 9,10-phenanthrenediamine: Effects of solvents and acid concentrations.
• Excited-state and ground-state proton-transfer reactions in 5-aminoindole.
• Effects of solvents and pH on the spectral behavior of 2-(p-aminophenyl)benzimidazole.

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