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首页> 外文期刊>RSC Advances >Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized tripodal molecular switch as a highly selective sequential pH sensor in aqueous solution
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Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized tripodal molecular switch as a highly selective sequential pH sensor in aqueous solution

机译：8-羟基喹啉功能化三脚架分子开关作为水溶液中高选择性顺序pH传感器的设计，合成和光物理性质

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摘要

The development and photophysical properties of a biomimetic analogue of microbial siderophore from quinolobactin have been described. The putative analogue, 5,5'-(2(((8-hydroxyquinolin-5-yl)-methylamino) methyl) 2-methylpropane-1,3-diyl)-bis(azanediyl)-bis(methylene) diquinolin-8-ol (TAME5OX), was synthesized with three bidentate 8-hydroxyquinoline (8HQ) groups, connected to a 1,1,1-tris( aminomethyl) ethane framework, and was selected for its potential applications in chemical and biological fields. A combination of absorption and emission spectrophotometry, potentiometry, electrospray mass spectrometry, NMR, IR and theoretical investigation was used to fully characterize TAME5OX. The intense fluorescence from TAME5OX is quenched intermittently under acidic and basic conditions due to the photoinduced intramolecular electron transfer from excited N-pyridyl to hydroxyl moiety of 8HQ units. This renders the ligand an OFF-ON-OFF type of pH-dependent fluorescent sensor. DFT was employed for optimization and evaluation of vibrational modes, excitation and emission properties of the protonated, neutral, deprotonated states of the analogue. Anomalous enhancement observed in the fluorescence spectra of the neutral form of the sensor can be attributed to subtle structural differences from its cationic and anionic forms. Plausible explanations for low fluorescence of the acidic as well as basic form are provided.
机译：已经描述了喹诺菌素的微生物铁载体的仿生类似物的发展和光物理性质。推定的类似物5,5'-（2（（（（（8-hydroxyquinolin-5-yl）-methylamino）methyl）甲基）2-甲基丙烷-1,3-二基）-双（氮杂二基）-双（亚甲基）二喹啉-8 -ol（TAME5OX）具有三个双齿8-羟基喹啉（8HQ）基团，连接到1,1,1-三（氨基甲基）乙烷骨架上，并被选择用于化学和生物领域。结合了吸收和发射分光光度法，电位计，电喷雾质谱，NMR，IR和理论研究来全面表征TAME5OX。来自TAME5OX的强荧光在酸性和碱性条件下间歇淬灭，这是由于光诱导的分子内电子从受激N-吡啶基转移到8HQ单元的羟基部分。这使配体成为依赖于pH的荧光传感器的OFF-ON-OFF类型。 DFT用于优化和评估类似物的质子化，中性，去质子态的振动模式，激发和发射性质。在传感器的中性形式的荧光光谱中观察到的异常增强可归因于与其阳离子和阴离子形式的细微结构差异。提供了对于酸性以及碱性形式的低荧光的合理解释。

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