Han Feng, Chi Lina, Liang Xiaofen, Ji Shaomin, Liu Shasha, Zhou Fuke, Wu Yubo, Han Keli, Zhao Jianzhang, James Tony D
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 158 Zhongshan Road, Dalian 116012, People's Republic of China.
J Org Chem. 2009 Feb 6;74(3):1333-6. doi: 10.1021/jo8025669.
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.
基于咔唑的双硼酸被发现是酒石酸的对映选择性荧光传感器。在中性pH条件下，该传感器对酒石酸对映体的荧光响应呈现增强/减弱现象。该传感器呈现出不寻常的荧光强度与pH值的关系，在酸性pH条件下发射减弱，而在碱性pH条件下发射增强。据推测，从荧光团到质子化胺/苯基硼酸单元的光致电子转移（PET）是造成这种效应的原因，密度泛函理论（DFT）计算对其进行了合理解释。
