Novel Soluble and Fluorescent Poly(arylene ether)s Containing p-Quaterphenyl, 2,5-Bis(4-phenylphenyl)oxadiazole, or 2,5-Bis(4-phenylphenyl)triazole Groups

Abstract

Three novel conjugated biphenols 3, 4, and 8 were synthesized by the Pd(OAc)2-catalyzed regioselective carbon-carbon coupling reaction of 2,6-di-tert-butylphenol or 2-phenylphenol with aryl halides. Although poly(arylene ether)s derived from biphenol 3 and arylene difluorides have low solubility in organic solvents, using 4,4′-(9-fluorenylidene)diphenol or 4,4′-(hexafluoroisopropylidene)diphenol as a comonomer gave soluble poly(arylene ether)s 6a-c. High molecular weight poly(arylene ether)s 7a′-c′ were also prepared from biphenol 4. The biscarbamate-masked monomers 5 and 9 improved the polymerization to give higher molecular weight polymers 7a-e and 10a-e in higher yields. Polymers 7 and 10 possess better film-forming capabilities and are still soluble in organic solvents. Polymers 6, 7, and 10 are all thermally stable with 5% weight loss temperatures higher than 500°C under nitrogen. The polymers show strong blue light emission ranging from 387 to 478 nm in solution, depending on the conjugated structure.

Synthesis and properties of sulfonated poly(arylene ether)s containing azole groups

“…Compounds 2 and 3 were synthesized by a modified method of Lu et al41 A 200 mL round‐bottomed flask equipped with nitrogen purge, condenser, and mechanical stirrer was charged with 1 (5.0 g, 19.4 mmol) and 20 mL of CHP. The mixture was heated at 150 °C to dissolve 1 .…”

“…Effect of heterocyclic groups has been explored. The azole groups are known to provide polymer membranes with excellent chemical and thermal stability in engineering polymers 39–41. Benzimidazole groups, for example, provide basic functionality as well as high thermal and mechanical stability.…”

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

“…Homo-and copoly(arylene ether)s containing the oxadiazole moiety synthesized with decafluorobiphenyl as a comonomer gave polymers with high Tg's and excellent thermal stability and showed blue light emission (22). 1,2,4-Triazole derivatives have also been widely applied as electron transport materials in electroluminescent cells.…”

Synthesis and properties of novel phosphorus‐containing poly(ether ether ketone ketone)s

“…Therefore, many efforts have been directed toward synthesizing soluble poly(ether ketone)s without scarification of their desired properties. Several approaches have been investigated to improve their solubility, such as the insertion of flexible linkages, the introduction of bulky pendent groups, and the incorporation of a noncoplanar structure into the polymer backbone 2–8…”