Colored Poly(arylene ether)s Containing Benzoylenebenzimidazole, Phthaloperinone, and Phthalocyanine Moieties

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.

11H-isoindolo[2,1-a]benzimidazoles (Review)

“…It is also necessary to mention papers on the practical application of isoindolo[2,1-a]benzimidazole derivatives as electrophotographic photoreceptors [128][129][130] and as additives for polymers [131]. Fluorescent compositions based on isoindolobenzimidazolone are described in the patent [132].…”

Fluorescent Poly(Arylene Ether)s with a 3,5‐Dipyridyl‐1,2,4‐triazole Pendent Group Joined by a N‐N Linkage

“…The polymerization reactions were conducted in NMP and sulpholane as solvent (12). A series of blue to greenish-yellow fluorescent poly (arylene ether)s with 3,5-diphenyl-1,2,4-triazole pendent group were synthesized with various activated difluoro monomers.…”

“…Poly(arylene ether)s containing the 1,3,5-triphenylbenzene moiety showed blue and red fluorescence (11). Colored and fluorescent poly(arylene ether)s containing benzoylenebenzimidazole, phthaloperinone and phthalocyanine moieties (12) and poly(imidoaryl ether)s with bulky pendent groups, blue light emiting poly(arylene ether)containing 3,6-dialkoxyphthalimide moieties were studied (13). A series of blue to greenish-yellow fluorescent, amorphous, thermally stable polymers were also prepared from a monomer with pendent 3,5-diphenyl-1,2,4-triazole groups (14).…”

Enhanced thermal properties of phthalonitrile networks by cooperating phenyl-s-triazine moieties in backbones

“…Since the condition of curing neat phthalonitriles was extremely sluggish [9], curing additives were utilized to accelerate the cross-linking reaction. Among kinds of curing additives, e.g., metals [10], metallic salts [11], organic acids [3c], phenols [12], amines [13], and bispropargyl ether [14], diamines are more extensively used [6a,15]. Two factors have been taken into account.…”