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

doi:10.1021/jo8025669

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

112 Citations (SciVal)

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 language	English
Pages (from-to)	1333-1336
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	74
Issue number	3
Early online date	14 Jan 2009
DOIs	https://doi.org/10.1021/jo8025669
Publication status	Published - 6 Feb 2009

Keywords

Electron transitions
Fluorescence
Sensors
Acids
Density functional theory

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10.1021/jo8025669

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

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.",

keywords = "Electron transitions, Fluorescence, Sensors, Acids, Density functional theory",

author = "Feng Han and Lina Chi and Xiaofen Liang and Shaomin Ji and Shasha Liu and Fuke Zhou and Yubo Wu and Keli Han and Jianzhang Zhao and James, \{Tony D\}",

year = "2009",

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doi = "10.1021/jo8025669",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - 3,6-Disubstituted carbazole-based bisboronic acids with unusual fluorescence transduction as enantioselective fluorescent chemosensors for tartaric acid

AU - Han, Feng

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

PY - 2009/2/6

Y1 - 2009/2/6

N2 - 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.

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.

KW - Electron transitions

KW - Fluorescence

KW - Sensors

KW - Acids

KW - Density functional theory

UR - https://www.scopus.com/pages/publications/64549104886

UR - http://dx.doi.org/10.1021/jo8025669

U2 - 10.1021/jo8025669

DO - 10.1021/jo8025669

M3 - Article

SN - 0022-3263

VL - 74

SP - 1333

EP - 1336

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

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

Abstract

Keywords

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