Synthesis of a series of metallophthalocyanine end-capped poly(aryl ether sulfone)s from a dicyanoarylene group containing biphenol

A novel biphenol monomer, 1,4-bis(4-hydroxy-phenyl)-2,3-dicyanonaphthlene was prepared in high yield in a two-step reaction from reduced phenolphthalein containing a hydro cyanic group by an improved method. A series of uncapped copolymers were synthesized using this bisphenol. In addition, a series of thermally stable poly(arylene ether)s having covalently bound metal (II) naphthalocyanine units were synthesized by the reaction of dicyanoarylene containing poly(aryl ether)s with excess amounts of 1,2-dicyanobenzene and the corresponding metal salt in quinoline. The copolymers synthesized had high glass transition temperature and exhibited good thermal stability. Also, these polymers were found to have good solubility and capable of forming tough films. These colored polymers showed visible absorption maxima in the range of 538–715 nm.