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Chemosensors 2017, 5(3), 26;

Fluorescence Chemosensory Determination of Cu2+ Using a New Rhodamine–Morpholine Conjugate

Department of Environmental Science, Faculty of Natural Resources, Tarbiat Modares University, Noor 46414-356, Iran
Department of Organic Chemistry, Faculty of Science, Tarbiat Modares University, Tehran 14155-4838, Iran
Department of Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar 47416-95447, Iran
Environmental Sciences Research Institute, Shahid Beheshti University, Tehran 1983969411, Iran
Fisheries and Aquaculture Department, College of Agriculture and Natural Resources, Persian Gulf University, Bushehr 75169, Iran
Author to whom correspondence should be addressed.
Received: 29 June 2017 / Revised: 21 August 2017 / Accepted: 23 August 2017 / Published: 19 September 2017
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A new rhodamine-B carbonyl-morpholine derivative (denoted as RECM) was prepared by a two-step synthesis procedure. The employed method allowed a lactam ring development of rhodamine-B and ethylenediamine to demonstrate a facile amide bond formation. The obtained RECM was confirmed by 1H NMR, 13C NMR, and mass spectrometry analysis. RECM was formed to detect copper ion (Cu2+) due to its problematic toxicity features in aquatic ecosystems. It showed a high selectivity toward Cu2+ in comparison with some environmentally relevant alkali, alkaline earth, and transition metal cations at 50 µM in acetonitrile. Moreover, non-fluorescent RECM showed fluorescence intensity and UV-Vis absorbance increases in the presence of Cu2+ with high linear dependent coefficients (R2 = 0.964 and R2 = 0.982 respectively) as well as a color change from colorless to pink owing to the ring opening of the rhodamine spirolactam form. Binding capability experiments presented a clear 1:1 stoichiometry of RECM–Cu2+ complex with the binding constant (Ka) as 2.25 × 104 M−1. The calculation of limits of detection (LOD) was 0.21 µM based on the linear regression method, which is below the maximum contaminant level goal (MCLG) value of Cu2+ (1.3 ppm equals to 20.46 µM) in drinking water. These characteristics make the RECM a promising candidate for the real-time detection of toxic Cu2+ in environmental monitoring applications. View Full-Text
Keywords: chemosensor; copper; rhodamine-B derivative; environmental monitoring chemosensor; copper; rhodamine-B derivative; environmental monitoring

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Shekari, Z.; Younesi, H.; Heydari, A.; Tajbakhsh, M.; Chaichi, M.J.; Shahbazi, A.; Saberi, D. Fluorescence Chemosensory Determination of Cu2+ Using a New Rhodamine–Morpholine Conjugate. Chemosensors 2017, 5, 26.

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