Journal of South China University of Technology (Natural Science Edition) ›› 2014, Vol. 42 ›› Issue (10): 90-94.doi: 10.3969/j.issn.1000-565X.2014.10.015

• Chemistry & Chemical Engineering • Previous Articles     Next Articles

A Fluorescent Probe for Visual Detection of Fluoride Ions

Yang Xiao-dong1  Wang Lei1  Lu Xin-wei2  Liu Rui-yuan2  Qu Jin-qing1   

  1. 1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, Guangdong, China; 2.  School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, Guangdong, China
  • Received:2014-04-28 Revised:2014-08-04 Online:2014-10-25 Published:2014-10-01
  • Contact: 瞿金清（1970-），男，教授，博士生导师 ，主要从事精细化学品的合成与应用研究。 E-mail:cejqqu@scut.edu.cn
  • About author:杨小东(1987-),男,博士,主要从事有机光电材料的合成研究.E-mail: xiaodyang@foxmail.com
  • Supported by:

    国家自然科学基金资助项目(21074073，51173050，21244007)

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Abstract:

2-(6-hydroxynaphthalen-2-methylene) malononitrile (probe 1) was synthesized by means of the reaction of malononitrile and 6-hydroxy-2-naphthaldehyde, and the product was used as a fluorescent probe for the detection of fluoride ions. The results show that, in the detection system, the DMSO solution of probe 1 is pale yellow without fluorescence, and it immediately turns to be pink with blue-fluorescence after adding fluoride ions but shows no fluorescence after adding other anions. It is also found that probe 1 exhibits a strong selectivity and a high sensitivity to fluoride ions. According to the evaluation of the Job’s plot, the ratio of probe 1 to fluoride ions in the complex is found to be 1:1. The 1H NMR titration results confirm that the deprotonation of phenolic hydroxyl of probe 1 occurs after adding fluoride ions. The calculation results based on the Frontier molecular orbital theory indicate that, after the deprotonation of probe 1, its HOMO–LUMO energy gap increases, and the solution color and the fluorescence spectrum change dramatically.

Key words: 2-(6-hydroxynaphthalen-2-methylene) malononitrile, fluoride ion, fluorescent probe