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

  • Özlem Özen Karakuş
  • Hasalettin Deligöz
Original Article

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 (18) 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.

Keywords

Calixarene Azocalix[4]arenes Di-substituted Diazo-coupling reaction Solvent effect Substituent effect Absorption spectra 

Notes

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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Copyright information

© Springer Science+Business Media B.V. 2008

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of Science–ArtsPamukkale UniversityDenizliTurkey

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