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A Fast, Convenient and Stable Fluorescent Probe for Detecting Fe3+/2+ and Its Applications

FOOD BIOSCIENCE(2024)

Beijing Technol & Business Univ

Cited 0|Views12
Abstract
A turn-on benzimidazole-based fluorescent probe (E)-2-((4-(5-bromo-1H-benzo[d]imidazol-2-yl)benzylidene)amino)phenol (BRAP) for the detection of Fe3+/2+ was developed. The probe BRAP was designed and synthesized using 2-hydroxyaniline as the recognition site and benzimidazole as the fluorophore. It was highly selective and sensitive with a detection limit as low as 2.1×10-8 mol/L and didn’t interfere with other analytes. Using EtOH: H2O (v:v=9:1) as the detection system, BRAP had non-fluorescence at 466 nm, which was mainly due to isomerization and rotation of the C=N bond. The dihedral angle rotation hindered the charge transfer between benzimidazole and 2-hydroxyaniline. However, upon the addition of Fe3+/2+, the C=N bond in probe BRAP was cleaved to form compound 3, whose electrons were transferred from the benzimidazole ring to the benzaldehyde portion upon excitation and showed blue fluorescence. In addition, the optimized structure and orbital energies of probe BRAP and its products were calculated by comparing three functional combinations with time-dependent density functional theory (TD-DFT) and the optimal functional and basis set [B3LYP /6-311+G(d,p)]. In addition, the probe BRAP combined with a smartphone was explored for the rapid detection of Fe3+/2+ in wine.
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Total iron,Turn -on,Probe,Wine,Fe3+/2+
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要点】:本文开发了一种基于苯并咪唑的荧光探针BRAP,用于快速、方便、稳定地检测Fe3+/2+,并应用于葡萄酒中铁离子的快速检测。

方法】:通过2-羟基苯胺作为识别位点,苯并咪唑作为荧光团,设计并合成了荧光探针BRAP。

实验】:在EtOH:H2O (v:v=9:1)检测系统中,BRAP在无Fe3+/2+存在时无荧光,加入Fe3+/2+后C=N键断裂,形成化合物3并表现出蓝色荧光。实验使用TD-DFT和[B3LYP /6-311+G(d,p)]基组计算了探针BRAP及其产物的优化结构和轨道能量。此外,利用BRAP探针结合智能手机对葡萄酒中的Fe3+/2+进行了快速检测,检测限低至2.1×10^-8 mol/L。