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Chemosensors 2017, 5(3), 26; https://doi.org/10.3390/chemosensors5030026

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

1
Department of Environmental Science, Faculty of Natural Resources, Tarbiat Modares University, Noor 46414-356, Iran
2
Department of Organic Chemistry, Faculty of Science, Tarbiat Modares University, Tehran 14155-4838, Iran
3
Department of Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar 47416-95447, Iran
4
Environmental Sciences Research Institute, Shahid Beheshti University, Tehran 1983969411, Iran
5
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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Abstract

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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