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. J Appl Polym Sci, 2011