Catechol Derivatives as Fluorescent Chemosensors for Wide-Range pH Detection
Catechol Derivatives as Fluorescent Chemosensors for Wide-Range pH Detection
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DOI：
10.1002/chem.200800722
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发表时间：
2008-01-01
影响因子：
4.3
通讯作者：
Ruiz-Molina, Daniel
中科院分区：
文献类型：
--
作者：
Evangelio, Emilia;Hernando, Jordi;Ruiz-Molina, Daniel
合成和表征的一个新的家庭邻苯二酚衍生物的设计行为作为荧光化学传感器的宽范围的pH值检测已被描述。这些化合物通过共价偶联邻苯二酚单元与其他芳环，从而获得具有pH响应性基团和荧光行为的π-离域系统。在吡啶-儿茶酚衍生物的情况下，这导致在有机介质中具有不同光学性质的多达三种不同的质子化状态，如密度泛函理论计算所证实的。通过应用双波长检测技术，该化合物在pH变化时显示互补的“关-开-关”和“开-关-开”发射曲线，这是一种可用于在宽pH范围内进行酸度检测的行为。
The synthesis and characterization of a new family of catechol derivatives designed to behave as fluorescent chemosensors for wide-range pH detection has been described. These compounds were prepared by covalently coupling a catechol unit with other aromatic rings, thus obtaining pi-delocalized systems with both pH-responsive groups and fluorescent behavior. In the case of a pyridine-catechol derivative, this leads to Up to three different protonation states with distinct optical properties in organic media, as corroborated by density functional theory calculations. By applying dual-wavelength detection techniques, this compound shows complementary "off- on-off" and "on-off-on" emission profiles upon pH variation, a behavior that call be exploited to perform acidity detection over a broad pH range.