Synthesis and characterization of tetrakis-derivatives of bisphenol-A with 4-phenylazoaniline and 5-(4-aminophenylazo)-25,26,27-tribenzoyloxy-28- hydroxycalix[4]arene

Abstract

The synthesis of tetrakis- derivatives of bisphenol-A containing azo groups at their 2,2',6,6'-positions is reported. Novel examples of bisphenol-A, coupled with diazonium salts and derived from 4-phenylazoaniline and 5-(4-aminophenylazo)-25,26,27-tribenzoyloxy-28-hydroxycalix [4]arene, have been synthesized. It has been observed that the coupling reaction of diazonium salt obtained from 4-phenylazoaniline with bisphenol-A gives tetrakis- while those derived from 5-(4-aminophenylazo)-25,26,27-tribenzoyloxy-28-hydroxycalix [4]arene give partially substituted bisphenol-A analogues. The newly prepared tetrakis-azo substituted bisphenol-A compounds (1 and 2) are characterized by using UV-vis, FT-IR, 1H-NMR spectroscopic methods as well as elemental analysis techniques. These azo compounds give rise to bathochromic shifts in the absorption spectra, which can even be detected by "naked eye." © 2011 Wiley Periodicals, Inc.