No abstract

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°C, 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.

High molecular weight phthalazinone containing poly(arylene ether)s, poly(arylene thioether)s, and poly(arylene sulfone)s with very high glass transition temperatures were synthesized from a series of new bisphthalazinone monomers. Bisphthalazinone monomers 7a−c and 8c were synthesized from 2-(4-chlorobenzoyl)benzoic acid in high yields. Poly(arylene ether)s and poly(arylene thioether)s were synthesized in N,N ‘ -dimethylacetamide (DMAc) in the presence of anhydrous K2CO3 by a nucleophilic substitution reaction between these bisphthalazinone monomers and activated difluoro compounds. The poly(arylene thioether)s were further oxidized to form poly(arylene sulfone)s, which would be very difficult, if not impossible, to synthesize by other method. All synthesized polymers have extremely high T gs and thermal stability as determined from DSC and TGA analysis. Poly(arylene sulfone)s have the highest T gs ranging from 288 to 333 °C. The poly(arylene ether)s and poly(arylene thioether)s described, having inherent viscosities in the range of 0.37−1.01 dL/g, are soluble in chlorinated solvents such as chloroform and could be cast into flexible films from solution. In contrast to their precursors, the poly(arylene sulfone)s described are not soluble in chloroform but are soluble in dipolar aprotic solvents such as DMAc.