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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Novel fluorescent probes for the fluoride anion based on hydroxy-substituted perylene tetra-(alkoxycarbonyl)
Fengxia Zhang1,2, Yunlong Zhao1, Yanhui Chi1
1College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education Shandong Provincial Key Laboratory of Clean Production of Fine Chemistry, Shandong Normal University Jinan 250014 P. R. China zshi@sdnu.edu.cn shijingmin1955@163.com.
Abstract:
The fluoride anion (F-) sensing abilities of 1-hydroxyl-3,4,9,10-tetra (n-butoxyloxycarbonyl) perylene (probe 1) and 1-hydroxyl-mono-five-membered S-heterocyclic annulated tetra (n-butoxyloxycarbonyl) perylene (probe 2) were studied through visual detection experiments, UV-Vis, fluorescence, and 1H NMR titrations. The probes were sensitive and selective for distinguishing F- from other anions (Cl-, Br-, I-, SO4 -, PF6 -, H2PO4 -, BF4 -, ClO4 -, OH-, CH3COO-, and HPO4 2-) through a change of UV-Vis and fluorescence spectra. The absorption and fluorescence emission properties of the probes arise from the intermolecular proton transfer (IPT) process between a hydrogen atom on the phenolic O position of probe and the F- anion. The sensing mechanism was supported by theoretical investigation. Moreover, probe-based test strips can conveniently detect F- without any additional equipment, and they can be used as fluorescent probes for monitoring F- in living cells.
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