The Design and Synthesis of Fluorescent Coumarin Derivatives and Their Study for Cu2+ Sensing with an Application for Aqueous Soil Extracts
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Váradi, L
Trinchi, A
Reichman, SM
Bao, L
Lan, M
Wei, G
Cole, IS
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Abstract
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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Molecules
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24
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19
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© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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Medicinal and biomolecular chemistry
Organic chemistry
Theoretical and computational chemistry
Cu2+ sensing
coumarin
fluorescent quenching
soil sensing
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Qian, B; Váradi, L; Trinchi, A; Reichman, SM; Bao, L; Lan, M; Wei, G; Cole, IS, The Design and Synthesis of Fluorescent Coumarin Derivatives and Their Study for Cu2+ Sensing with an Application for Aqueous Soil Extracts, Molecules, 2019, 24 (19), pp. 3569: 1-3569: 17