The Design and Synthesis of Fluorescent Coumarin Derivatives and Their Study for Cu2+ Sensing with an Application for Aqueous Soil Extracts

Autor: Bin Qian, Linda Váradi, Adrian Trinchi, Suzie M. Reichman, Lei Bao, Minbo Lan, Gang Wei, Ivan S. Cole
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Molecules, Vol 24, Iss 19, p 3569 (2019)
Druh dokumentu: article
ISSN: 1420-3049
24193569
DOI: 10.3390/molecules24193569
Popis: A series of fluorescent coumarin derivatives 2a−e were systematically designed, synthesized and studied for their Cu2+ sensing performance in aqueous media. The sensitivities and selectivities of the on-to-off fluorescent Cu2+ sensing signal were in direct correlation with the relative arrangements of the heteroatoms within the coordinating moieties of these coumarins. Probes 2b and 2d exhibited Cu2+ concentration dependent and selective fluorescence quenching, with linear ranges of 0−80 μM and 0−10 μM, and limits of detection of 0.14 μM and 0.38 μM, respectively. Structural changes of 2b upon Cu2+ coordination were followed by fluorescence titration, attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR), mass spectrometry, and single crystal X-ray diffraction on the isolated Cu2+-coumarin complex. The results revealed a 1:1 stoichiometry between 2b and Cu2+, and that the essential structural features for Cu2+-selective coordination are the coumarin C=O and a three-bond distance between the amide NH and heterocyclic N. Probe 2b was also used to determine copper (II) levels in aqueous soil extracts, with recovery rates over 80% when compared to the standard soil analysis method: inductively coupled plasma-mass spectrometry (ICP-MS).
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