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Azocalixarenes: Synthesis, Characterization, Complexation, Extraction, Absorption Properties and Thermal Behaviours

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Abstract

Azocalixarenes, which have a conjugated chromophore azo (–N=N–) group in p-positions, are synthesized in “one-pot” procedures in satisfactory yields. Their structures in the solid and solution are elucidated by UV–vis, FT-IR, 1H and 13C NMR spectroscopic methods as well as elemental analysis techniques. Some of them are complexed with metal ions (alkali, alkaline-earth and transition metal ions) under neutral conditions. A wide variety of applications is expected by the functionalization of the side arms. The selective liquid–liquid extraction of various alkali, alkaline-earth and transition metal cations from the aqueous phase to the organic phase is carried out by using azocalixarenes. Furthermore, the synthesized azocalixarenes are utilized for selective extraction of Fe3+ cations from the aqueous phase to the organic phase. The effects of varying pH and solvent upon the absorption ability of azocalixarenes substituted with electron-donating and electron-withdrawing groups at their o-, m-, p-positions are examined. The thermal behaviours of azocalixarenes containing upper rim functionalized groups are investigated by means of thermogravimetry (TG), differential thermal analysis (DTA) and differential thermogravimetry (DTG).

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Acknowledgements

The author is grateful to Professor Mustafa Yılmaz (Selçuk University, Faculty of Science-Arts, Department of Chemistry, Konya, Turkey) for encouragement of this work. The author also thanks Prof. Halil Çetişli for DTA/DTG spectroscopic analyses, and Dr. İzzet Şener (Pamukkale University, Faculty of Science-Arts, Department of Chemistry, Denizli, Turkey) for collaborations.

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  1. Faculty of Science-Arts, Department of Chemistry, Pamukkale University, 20017, Denizli, Turkey

    Hasalettin Deligöz

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Deligöz, H. Azocalixarenes: Synthesis, Characterization, Complexation, Extraction, Absorption Properties and Thermal Behaviours. J Incl Phenom Macrocycl Chem 55, 197–218 (2006). https://doi.org/10.1007/s10847-006-9096-z

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