Poly(imino ketone)s as New High-Performance Polymers

A series of novel poly(imino ketone)s (PIK) have been synthesized via palladium-catalyzed polycondensation (Hartwig−Buchwald reaction) of aromatic dichloro or dibromo ketones with various aromatic diamines. The influence of the halogen-containing monomers, concentration, temperature, and catalyst ligands on the polycondensation reaction and on the polymer polydispersity was investigated. These polymers showed good thermal stability with high decomposition temperatures. FT-IR spectra of the PIKs revealed that in the solid state intermolecular and intramolecular hydrogen bonding (N−H···OC) are present. A model compound was synthesized and characterized by standard spectroscopic methods in order to assist in the structure proof of the polymer. The mechanical behavior of the PIK polymers suggests that they can be considered as a new class of high-performance polymers.