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Synthesis and characterization of a chemosensor based on trisamidetetraazocalix[4]arene linked by melamine

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Abstract

In this study, azocalix[4]arene was prepared by linking 4-methylaniline to calix[4]arene through a diazo-coupling reaction, and the targeted amide derivative was synthesized with the help of its monoester, monoacid, and monoacid chloride derivatives, respectively. The synthesis and characterization of novel trisamidetetraazocalix[4]arene [2,4,6-tris(25-aminocarbonylmethoxy-26,27,28-trihydroxy-5,11,17,23-tetrakis(4-methylphenyl)azocalix[4]arene)-1,3,5-triazine] were prepared by reacting 25-(chloroformylmethoxy)-26,27,28-trihydroxy-5,11,17,23-tetrakis(4-methylphenyl)azocalix[4]arene and melamine (2,4,6-triamino-1,3,5-triazine) to an amide formation reaction. This compound was characterized by elemental analysis, 1H NMR, IR and mass spectrometry. Picrate extraction studies were carried out from the aqueous phase to the chloroform phase with selected metal ions (K+, Sr2+, Ag+, Hg+, Hg2+, Co2+, Ni2+, Cu2+, Pb2+, Cr3+, Al3+) of the title compound. Trisamidetetraazocalix[4]arene showed extraction value in decreasing order against Hg2+ > Hg+ > Ag+ > Cr3+ > Al3+ from selected metals and showed the highest extraction value (66.2%) in Hg2+ ion.

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Acknowledgements

The authors would like to thank Afyon Kocatepe University for its support.

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Authors and Affiliations

  1. Faculty of Engineering, Department of Chemical Engineering, Afyon Kocatepe University, 03200, Afyonkarahisar, Turkey

    Serkan Elçin & Resul Gönül

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  1. Serkan Elçin
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  2. Resul Gönül
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Correspondence to Serkan Elçin.

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Elçin, S., Gönül, R. Synthesis and characterization of a chemosensor based on trisamidetetraazocalix[4]arene linked by melamine. Monatsh Chem 154, 331–337 (2023). https://doi.org/10.1007/s00706-023-03045-8

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