Synthesis of Poly(arylene ether amine)s from a Monomer Containing an Electron‐Donating Amine Group in a Nucleophilic Aromatic Substitution Reaction

Abstract

Summary: Poly(arylene ether amine)s were synthesized by a nucleophilic aromatic substitution polycondensation of bis[4‐fluoro‐3‐(trifluoromethyl)phenyl]amine with several bisphenols. Even though the monomer has an electron‐donating diphenylamine moiety, which normally deactivates a nucleophilic aromatic substitution (SNAr) reaction, the polymerization proceeded by a SNAr reaction to give high‐molecular‐weight polymers. The polymers show good solubility in common organic solvents and have Tgs in the range of 123 °C to 177 °C.High‐molecular‐weight poly(arylene ether amine)s synthesized by a SNAr reaction with the monomer containing an electron‐donating diphenylamine moiety.imageHigh‐molecular‐weight poly(arylene ether amine)s synthesized by a SNAr reaction with the monomer containing an electron‐donating diphenylamine moiety.

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

“…Poly(arylene ether)s have been widely used as engineering thermoplastics due to their good mechanical properties, high thermal stability, and excellent resistance to hydrolysis and oxidation reaction . The known approaches for the synthesis of poly(arylene ether)s include electrophilic aromatic substitution, nucleophilic aromatic substitution, and metal catalyzed coupling reactions. − Among these methods, the nucleophilic aromatic substitution (S N Ar) reaction is the most practical method for the preparation of poly(arylene ether)s despite the fact that it requires some structural features, leaving group activated with electron withdrawing groups. , Various heterocyclic rings and electron withdrawing groups such as sulfone, ketone, and imide groups have been used as an activating group for S N Ar reactions to produce high-molecular-weight poly(arylene ether)s. − Trifluoromethyl groups are also useful for S N Ar reactions to activate fluoro or nitro groups for displacement by phenoxides. − …”