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HBT-based chemosensors for the detection of fluoride through deprotonation process: experimental and DFT studies

机译：基于HBT的化学传感器通过去质子化过程检测氟化物：实验和DFT研究

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When searching to develop fluoride chemosensors based on O-H center dot center dot center dot F, we discovered that an HBT-based fluorophore containing a hydroxyl group was easily synthesized and displayed excellent fluorescence properties. 4-(benzothiazol-2-yl)-phenol ((LH)-H-1) was found to facilitate the monitoring of fluoride and showed ratiometric fluorescence changes. It is worth noting that an aldehyde group in conjugation with the HBT-based fluorophore core at an adjacent position to the hydroxyl group (i.e. 5-(benzothiazol-2-yl)-2-hydroxybenzaldehyde, (LH)-H-2) would elevate the sensitivity towards fluoride immensely. Spectroscopic studies indicated that (LH)-H-1 and (LH)-H-2 interacted with a fluoride anion, which involved a two-step reaction: hydrogen bond formation and deprotonation. Deprotonation of the chemosensors by a fluoride anion enhanced the electron-donating ability of the phenolic O- to the HBT core acceptor and facilitated an intramolecular charge transfer process, resulting in a red shift in both UV-vis absorption and fluorescence spectra. The mechanism of (LH)-H-2 binding with fluoride was confirmed by H-1 NMR titration experiments and DFT computational calculations.
机译：在研究开发基于O-H中心点中心点中心点中心点F的氟化物化学传感器时，我们发现含有羟基的HBT基荧光团很容易合成，并显示出优异的荧光性能。发现4-（苯并噻唑-2-基）-苯酚（（LH）-H-1）有助于监测氟化物，并显示出比例荧光变化。值得注意的是，与羟基相邻的HBT基荧光团核心共轭的醛基（即5-（苯并噻唑-2-基）-2-羟基苯甲醛，（LH）-H-2）大大提高了对氟化物的敏感性。光谱研究表明（LH）-H-1和（LH）-H-2与氟阴离子相互作用，这涉及两步反应：氢键形成和去质子化。氟化物阴离子使化学传感器去质子化，增强了酚类O-对HBT核心受体的供电子能力，并促进了分子内电荷转移过程，导致UV-vis吸收和荧光光谱发生红移。通过H-1 NMR滴定实验和DFT计算计算，证实了（LH）-H-2与氟化物的结合机理。

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