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Synthesis of Two Novel Water-Soluble Iron Phthalocyanines and Their Application in Fast Chromogenic Identification of Phenolic Pollutants

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Abstract

The novel water-soluble and sterically hindered phthalocyanine complexes, i.e. iron(III) tetra-(4-carboxyphenoxy)phthalocyanine (3) and iron(III) tetra-(8-quinolineoxy-5-sulfonicacid)phthalocyanine (4) were synthesized for fast detection of phenolic pollutants. These two FePc complexes exhibited the high catalytic activity in the chromogenic reactions of phenolic pollutants. Five phenolic substrates, including phenol, 2-chlorophenol, 4-chlorophenol, 2,4-dichlorophenol and 1-naphthol could be efficiently oxidized by tert-butyl hydroperoxide in the presence of these selected FePc catalyst. UV–Vis spectroscopy and HPLC technique were used to monitor the catalyzed oxidation of phenolic substrates. Compared with catalytic methods by other reported phthalocyanines, this system has the obvious advantages of fast oxidation and high-yield conversion of phenolic substrates. Under the optimal conditions, the chromogenic process of 2-chlorophenol could be completed just within 10 min with more than 90 % of conversion. Potentially, this system is promising for the application of fast chromogenic identification of phenolic pollutants.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 61377092 and 51302241), the Fundamental Research Funds for the Central Universities (WUT: 2013-IV-010), the Science and Technology Key Project of Education Department of Henan Province (No. 13B430233 and No. 13A150743). We thank professor Yu Cao (College of Chemistry, Huazhong Normal University) for the help of chemical characterization and measurement. We thank MSc Shilong Zhao (School of Materials Science and Engineering, Wuhan University of Technology) for the help of purification of two novel water-soluble iron phthalocyanines.

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Authors and Affiliations

  1. National Engineering Laboratory for Fiber Optic Sensing Technology, Key Laboratory of Fiber Optic Sensing Technology and Information Processing (Ministry of Education), Wuhan University of Technology, Wuhan, 430070, People’s Republic of China

    Jingjing Gong, Jun Huang, Liyun Ding, Yilin Tong, Kun Li & Cong Zhang

  2. Key Laboratory for Micro-Nano Energy Storage and Conversion Materials of Henan Province, School of Chemistry and Chemical Engineering, Institute of Surface Micro and Nano Materials, Xuchang University, Henan, 461000, People’s Republic of China

    Dapeng Li

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  1. Jingjing Gong
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  2. Dapeng Li
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  3. Jun Huang
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  4. Liyun Ding
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  5. Yilin Tong
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  6. Kun Li
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  7. Cong Zhang
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Corresponding author

Correspondence to Jun Huang.

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Gong, J., Li, D., Huang, J. et al. Synthesis of Two Novel Water-Soluble Iron Phthalocyanines and Their Application in Fast Chromogenic Identification of Phenolic Pollutants. Catal Lett 144, 487–497 (2014). https://doi.org/10.1007/s10562-013-1178-0

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  • DOI: https://doi.org/10.1007/s10562-013-1178-0

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