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Asymmetrically substituted 5,5′′-diaryl-2,2′:6′,2′′-terpyridines as efficient fluorescence “turn-on” probes for Zn2+ in food/cosmetic samples and human urine
Journal of Photochemistry and Photobiology A: Chemistry ( IF 4.3 ) Pub Date : 2020-12-17 , DOI: 10.1016/j.jphotochem.2020.113101
Olga V. Shabunina , Ekaterina S. Starnovskaya , Yaroslav K. Shaitz , Dmitry S. Kopchuk , Leila K. Sadieva , Grigory A. Kim , Olga S. Taniya , Igor L. Nikonov , Sougata Santra , Grigory V. Zyryanov , Valery N. Charushin

The present article describes the synthesis of new asymmetrically substituted 5,5′′-diaryl-2,2′:6′,2′′–terpyridines as prospective chemosensors/probes for the fluorescence “turn-on” detections of Zn2+. After the fluorescence titration experiments two most representative terpyridines, namely 4-phenyl-1-(6-(4-p-tolyl-6,7-dihydro-5H-cyclopenta[c]-pyridin-1-yl)pyridin-2-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine and 5-phenyl-5′′-p-tolyl-2,2′:6′,2′′-terpyridine were selected based on high binding constant up to 106 M−1 for the 1:2 (Zn2+ : ligand) complexes along with the limits of detection (LOD) as low as ∼0.1 × 10-9 M. These ligands have been further used as fluorescence probes for the qualitative and quantitative detection of Zn2+ in real samples, such as food/cosmetic samples and human urine. For all the samples, these probes exhibited an intensive fluorescence enhancement via the effective transduction LE-TICT-switching signal. The stoichiometry and structure of the Zn2+ complexes were supported by DFT calculations and 1H NMR experiments.



中文翻译:

不对称取代的5,5''-二芳基-2,2':6',2''-吡啶并用作食品/化妆品样品和人类尿液中Zn 2+的有效荧光“开启”探针

本文描述了新的不对称取代的5,5''-二芳基-2,2':6',2''-三联吡啶的合成,作为预期的化学传感器/探针,用于Zn 2+的荧光“开启”检测。经过荧光滴定实验后,两个最有代表性的三联吡啶为:4-苯基-1-(6-(4-甲苯基-6,7-二氢-5 H-环戊[ c ]-吡啶-1-基)吡啶-2 (-基)-6,7-二氢-5 H-环戊基[ c ]吡啶和5-苯基-5''-甲苯基-2,2':6',2''-吡啶是基于高结合力而选择的常数高达10 6中号-1为1:2(锌2+:配体)以及低至〜0.1×10 -9 M的检出限(LOD)。这些配体还被用作荧光探针,用于定性和定量检测真实样品(例如食品)中的Zn 2+ /化妆品样品和人尿。对于所有样品,这些探针均通过有效的LE-TICT转换信号转导显示出强烈的荧光增强。DFT计算和1 H NMR实验证实了Zn 2+配合物的化学计量和结构。

更新日期:2021-01-02
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