3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid

Feng Han, Lina Chi, Xiaofen Liang, Shaomin Ji, Shasha Liu, Fuke Zhou, Yubo Wu, Keli Han, Jianzhang Zhao, Tony D James

Research output: Contribution to journalArticle

106 Citations (Scopus)

Abstract

Carbazole-based bisboronic acids were found to be enanti-oselective fluorescent sensors for tartaric acid. The fluorescence response toward the enantiomers of tartaric acid at neutral pH displayed enhancement/diminishment. The sensor displays an unusual fluorescence intensity-pH relationship with diminished emission at acidic pH but enhanced emission at basic pH. Photoinduced electron transfer (PET) from the fluorophore to the protonated amine/phenylboronic acid unit is proposed to be responsible for this effect, which is rationalized by density functional theory (DFT) calculations.
Original languageEnglish
Pages (from-to)1333-1336
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number3
Early online date14 Jan 2009
DOIs
Publication statusPublished - 6 Feb 2009

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Fluorescence
Acids
Enantiomers
Fluorophores
Sensors
Amines
Density functional theory
Electrons
tartaric acid
carbazole
benzeneboronic acid

Keywords

  • Electron transitions
  • Fluorescence
  • Sensors
  • Acids
  • Density functional theory

Cite this

3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid. / Han, Feng; Chi, Lina; Liang, Xiaofen; Ji, Shaomin; Liu, Shasha; Zhou, Fuke; Wu, Yubo; Han, Keli; Zhao, Jianzhang; James, Tony D.

In: Journal of Organic Chemistry, Vol. 74, No. 3, 06.02.2009, p. 1333-1336.

Research output: Contribution to journalArticle

Han, Feng ; Chi, Lina ; Liang, Xiaofen ; Ji, Shaomin ; Liu, Shasha ; Zhou, Fuke ; Wu, Yubo ; Han, Keli ; Zhao, Jianzhang ; James, Tony D. / 3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 3. pp. 1333-1336.
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AU - Chi, Lina

AU - Liang, Xiaofen

AU - Ji, Shaomin

AU - Liu, Shasha

AU - Zhou, Fuke

AU - Wu, Yubo

AU - Han, Keli

AU - Zhao, Jianzhang

AU - James, Tony D

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AB - Carbazole-based bisboronic acids were found to be enanti-oselective fluorescent sensors for tartaric acid. The fluorescence response toward the enantiomers of tartaric acid at neutral pH displayed enhancement/diminishment. The sensor displays an unusual fluorescence intensity-pH relationship with diminished emission at acidic pH but enhanced emission at basic pH. Photoinduced electron transfer (PET) from the fluorophore to the protonated amine/phenylboronic acid unit is proposed to be responsible for this effect, which is rationalized by density functional theory (DFT) calculations.

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KW - Sensors

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