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An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent

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Abstract

A facile synthesis procedure, whereby 9-Anthraldehyde (AA) is coupled to aminated rhodamine (AR) via a Schiff base-type reaction, is reported. The applicability and performance of the obtained material (AA-AR) as a sensing agent was studied towards 16 metal cations (i.e. Li+, Na+, Ag+, Ca2+, Ba2+, Co2+, Cs+, Cu2+, Mg2+, Hg2+, Mn2+, Pb2+, Ni2+, Sr2+, Zn2+, Al3+). Among the studied metals, an extraordinary selectivity was observed for Hg2+, and the observed selectivity was found not to be influenced by the presence of other cations and some common anions (i.e. Br−, Cl−, I−, HPO42−, H2PO4−, NO3−, NO2−, ClO4−, AcO−, HSO4−, SO42−, Cr2O7−, CO32−, OH− and HCO3−). The material, AA-AR, exhibited such a high selectivity and sensitivity towards Hg2+ that it could be detected even by naked eyes. The Hg2+-sensing property of AA-AR was found not to be limited to colorimetric detections so that a high fluorescent nature of the compound was also observed upon binding Hg2+ ion. The detection limit, which is correspondent to fluorescence emission intensity, was found as 0.87 μM. The underlying mechanism of sensing property was studied by using some spectroscopic techniques such as FT-IR, 1H-NMR, 13C-NMR, and UV-Vis. (Job-plot). In the final course of the experiments, the performance of AA-AR in cell-imaging was also studied, and even trace amounts of Hg2+ in living cells could be detected by the studied probe. Thus, the applicability of a new synthesis approach in producing a highly efficient new fluorescence sensor for the detection of Hg2+ ions is discussed in detail.

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Change history

  • 04 December 2019

    The original version of this article unfortunately contained a mistake. The presentation of Scheme 1 was incorrect as the word "modifified" should be written as "modified" and the abbreviation "CS-F" should be replaced by "AA-AR".

  • 04 December 2019

    The original version of this article unfortunately contained a mistake. The presentation of Scheme 1 was incorrect as the word "modifified" should be written as "modified" and the abbreviation "CS-F" should be replaced by "AA-AR".

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Acknowledgments

Authors wish to thank Karamanoglu Mehmetbey University (Karaman, Turkey), and Nigde Ömer Halisdemir University (Nigde, Turkey) for the facilities provided.

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Authors and Affiliations

  1. Faculty of Engineering, Department of Bioengineering, Karamanoglu Mehmetbey University, Karaman, Turkey

    Fulya Cicekbilek, Bahar Yilmaz & Mevlut Bayrakci

  2. Faculty of Science and Arts, Chemistry Department, Nigde Ömer Halisdemir University, 51240, Nigde, Turkey

    Orhan Gezici

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  1. Fulya Cicekbilek
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  2. Bahar Yilmaz
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Correspondence to Mevlut Bayrakci or Orhan Gezici.

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Cicekbilek, F., Yilmaz, B., Bayrakci, M. et al. An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent. J Fluoresc 29, 1349–1358 (2019). https://doi.org/10.1007/s10895-019-02462-5

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