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Azocalixarenes.8: synthesis and investigation of the absorption spectra of di-substituted azocalix[4]arenes containing chromogenic groups

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Abstract

The synthesis of series of chromogenic di-substituted azocalix[4]arene derivatives is described. A ketone moiety as a different chelating agent is grafted on the lower rim of p-tert-butylcalix[4]arenes. Eight novel azocalix[4]arenes (1–8) are prepared by linking 2-, 3- and 4-nitroaniline, 4-phenylazoaniline, 3- and 4-chloroaniline or 2- and 4-methylaniline to 25,27-diacetonyloxy-26,28-dihydroxy-11,23-di-(tert-butyl)calix[4]arene through a diazo-coupling reaction, and characterized by UV–Vis, FT-IR and 1H-NMR spectroscopic techniques and elemental analysis, consecutively. The absorption spectra of the di-substituted azocalix[4]arenes are discussed, according to effect of varying pH and solvent upon the absorption ability of azocalix[4]arenes. The colors of these azocalix[4]arenes are compared with respect to nature of their aromatic rings and substituents there in. Concentration effects on the visible absorption maxima of these compounds are also reported.

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Acknowledgements

This work was supported in part by a grant from the Scientific Research Projects Council of Pamukkale University (PA.U. BAP, 2003/023). The authors would like to express their thanks to Prof. Alaattin ŞEN for his critical reading of draft manuscript and making many helpful suggestions and corrections.

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

    Özlem Özen Karakuş & Hasalettin Deligöz

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  1. Özlem Özen Karakuş
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  2. Hasalettin Deligöz
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Correspondence to Hasalettin Deligöz.

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Karakuş, Ö.Ö., Deligöz, H. Azocalixarenes.8: synthesis and investigation of the absorption spectra of di-substituted azocalix[4]arenes containing chromogenic groups. J Incl Phenom Macrocycl Chem 61, 289–296 (2008). https://doi.org/10.1007/s10847-008-9421-9

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