A selective N,N-dithenoyl-rhodamine based fluorescent probe for Fe3+ detection in aqueous and living cells

  • J Environ Sci (China). 2020 Apr:90:180-188. doi: 10.1016/j.jes.2019.12.005.
Yi Liu  1 ,  Cuixia Zhao  2 ,  Xiangyun Zhao  3 ,  Huili Liu  4 ,  Yibin Wang  5 ,  Yuguo Du  6 ,  Dongbin Wei  7
Affiliations
  • 1. School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China. Electronic address: [email protected].
  • 2. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
  • 3. School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China.
  • 4. Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Yantai University, Yantai 264005, China.
  • 5. Key Laboratory of Marine Ecology and Environmental Science and Engineering, First Institute of Oceanography, Ministry of Natural Resources (China), Qingdao 266061, China.
  • 6. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China. Electronic address: [email protected].
  • 7. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China. Electronic address: [email protected].
PMID: 32081314 DOI: 10.1016/j.jes.2019.12.005
Abstract

A novel N,N-dithenoyl-rhodamine based fluorescent and colorimetric Fe3+ probe 1 was designed and synthesized by only one step from Rhodamine B hydrazide and 2-thiophenecarbonyl chloride. The structure of probe 1 was characterized by 1H NMR/13C NMR spectroscopy, IR spectroscopy, and HRMS spectrometry. Accompanying with significant changes in visual color and fluorescent spectrum, probe 1 displayed good sensitivity for Fe3+ with an abroad pH span. The detection limit (3.76 μmol/L, 0.2 mg/L) for Fe3+ was lower than WHO recommended value (0.3 mg/L) for drinking water. Using two thiophene carbonyl groups as coordinating functional recognition group, probe 1 showed excellent selectivity towards Fe3+ over diverse coexistent metal ions and anions. The sensing mechanism between dithenoyl-substituted probe 1 and Fe3+ was further confirmed by 1H NMR and IR titration experiments, binding constants study, and Job's plot analysis. Furthermore, probe 1 also exhibited good cell membrane permeability and could be used as an efficient Fe3+ probe in living human cells.

Keywords
Cell imaging; Fe(3+) determination; Fluorescent probe; N,N-dithenoyl-rhodamine; Turn-on.
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