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

Original Article


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.


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



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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© Springer Science+Business Media B.V. 2008

Authors and Affiliations

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

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