Selectivity tune of fluoride ion sensing for phenolic OH-containing BODIPY dyes

Selectivity tune of fluoride ion sensing for phenolic OH-containing BODIPY dyes
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含酚 OH 的 BODIPY 染料氟离子传感的选择性调谐

DOI:
10.1016/j.snb.2011.05.027
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发表时间:
2011-10
影响因子:
8.4
通讯作者:
Hou, Yuanjun
Hou, Yuanjun
中科院分区:
化学1区
文献类型:
--
作者:
Wang, Xuesong;Wang, Jianguang;Zhang, Baowen;Li, Chao;Hou, Yuanjun

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设计并合成了一系列在间位苯基上带有酚羟基的BODIPY染料,通过O-H-F氢键作用对F−离子进行比色和荧光检测。邻苯基骨架上的供电子基团(如甲氧基和叔丁基)以及酚羟基的取代位置对OH的化学位移、pKa和OH与F−的结合常数都有显著影响。通过结构优化下调与F−的结合常数,可以大大提高对F −的结合选择性。因此,BODIPY 7可以在乙腈中以吸收和荧光模式选择性地探测F−,并且不响应包括AcO−在内的其他阴离子。所观察到的结合选择性的结构依赖性可以为开发新的高选择性的F−比色或荧光传感器提供指导。
A series of BODIPY dyes bearing phenolic OH in themeso-phenyl moiety were designed and synthesized for colorimetric and fluorescent detection of F−ions by way of O–H⋯F hydrogen bonding interactions. Both the electron-donating group attached on themeso-phenyl skeleton, such as methoxy group andt-butyl group, and the substituting position of the phenolic OH have dramatic influences on the chemical shift of OH, pKaof OH, and the binding constant of OH to F−. The binding selectivity to F−over other anions may be greatly improved by down-regulating the binding constant to F−through structure optimization. As a result, BODIPY7can selectively probe F−in both absorption and fluorescence modes in acetonitrile and does not response to other anions including AcO−. The observed structure dependence of the binding selectivity may provide guidelines for the development of new F−colorimetric or fluorescent sensors of high selectivity.
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