Azocalixarenes.8: synthesis and investigation of the absorption spectra of di-substituted azocalixarenes containing chromogenic groups
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The synthesis of series of chromogenic di-substituted azocalixarene derivatives is described. A ketone moiety as a different chelating agent is grafted on the lower rim of p-tert-butylcalixarenes. Eight novel azocalixarenes (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)calixarene 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 azocalixarenes are discussed, according to effect of varying pH and solvent upon the absorption ability of azocalixarenes. The colors of these azocalixarenes 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.
KeywordsCalixarene Azocalixarenes 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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