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Charge-Transfer-Induced Fluorescence Quenching of Anthracene Derivatives and Selective Detection of Picric Acid

机译:电荷转移诱导蒽衍生物的荧光猝灭和苦味酸的选择性检测

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摘要

2,6-Divinylpyridine-appended anthracene derivatives flanked by two alkyl chains at the 9,10-position of the core have been designed, synthesized, and characterized by NMR, MALDI-TOF, FTIR, and single-crystal XRD. These anthracene derivatives are able to recognize picric acid (2,4,6-trinitrophenol, PA) selectively down to parts per billion (ppb) level in aqueous as well as nonaqueous medium. Fluorescence emission of these derivatives in solution is significantly quenched by adding trace amounts of PA, even in the presence of other competing analogues, such as 2,4-dinitrophenol (2,4-DNP), 4-nitrophenol (NP), nitrobenzene (NB), benzoic acid (BA), and phenol (PH). The high sensitivity of these derivatives toward PA is considered as a combined effect of the proton-induced intramolecular charge transfer (ICT) as well as electron transfer from the electron-rich anthracene to the electron-deficient PA. Moreover, visual detection of PA has been successfully demonstrated in the solid state by using different substrates.
机译:已经设计,合成并通过核磁共振,MALDI-TOF,FTIR和单晶XRD对2,6-二乙烯基吡啶加成的蒽衍生物进行了侧翼设计,该衍生物侧接在芯的9,10位上的两个烷基链上。这些蒽衍生物能够在水性和非水性介质中选择性地识别低至十亿分之一(ppb)含量的苦味酸(2,4,6-三硝基苯酚,PA)。即使存在其他竞争性类似物,例如2,4-二硝基苯酚(2,4-DNP),4-硝基苯酚(NP),硝基苯( NB),苯甲酸(BA)和苯酚(PH)。这些衍生物对PA的高敏感性被认为是质子诱导的分子内电荷转移(ICT)以及电子从富电子蒽向电子贫乏PA转移的综合作用。而且,已经通过使用不同的底物成功地证明了在固态下对PA的视觉检测。

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