Colored poly(arylene ether)s containing benzoylenebenzimidazole, phthaloperinone, and phthalocyanine moieties

The synthesis of a novel biphenol from phenolphthalein that contains an anhydride group is described. The biphenol readily undergoes further reactions. Two biphenols that contain the 1,2-benzoylenebisbenzimidazole or phthaloperin-12-one moiety, respectively, were prepared from the biphenol anhydride by reaction with aromatic diamines, o-phenylenediamine, and 1,8-diaminonaphthalene. Two series of poly(arylene ether)s were synthesized from these heterocyclic containing biphenols. The polymers and copolymers synthesized exhibited extremely high glass transition temperatures and excellent thermooxidative stability. The highest T-g and 5% weight loss temperatures of these polymers were almost 360 and 600 degreesC, respectively. The two series of poly(arylene ether)s were yellow and orange in color, respectively. These poly(arylene ether)s have good solubility and can be cast from solution into tough films. The glass transition temperatures of the copolymers increased with increasing heterocycle content, while the solubilities decreased. We have also synthesized, utilizing a biphenol containing the dicyanoarylene moiety, a polymer that contains the phthalocyanine copper(II) moiety that has a blue color. Copolymers containing all three moieties have been synthesized that have a permanent black color since they absorb over the entire visible spectral region from 300 to 750 nm. All of the polymers were highly fluorescent materials with emission wavenumbers ranging from 400 to 750 nm.