3,6-Disubstituted Carbazole-Based Bisboronic Acids with Unusual Fluorescence Transduction as Enantioselective Fluorescent Chemosensors for Tartaric Acid

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• 作者：Feng Han ; Lina Chi ; Xiaofen Liang ; Shaomin Ji ; Shasha Liu ; Fuke Zhou ; Yubo Wu ; Keli Han ; Jianzhang Zhao ; Tony D. James
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：February 6, 2009
• 年：2009
• 卷：74
• 期：3
• 页码：1333-1336
• 全文大小：256K
• 年卷期：v.74,no.3(February 6, 2009)
• ISSN：1520-6904

文摘

Carbazole-based bisboronic acids were found to be enantioselective 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.