Hyperbranched poly(ether ketone) analogues with heterocyclic triazine moiety: Synthesis and peripheral functionalization

Hyperbranched poly(ether ketone) with 1,3,5-s-triazine moiety was prepared by a one pot polymerization of an AB₂ type monomer, 2,4-bis(4-hydroxy- phenyl)-6-(4-(4-(4-fluorobenzoyl)phenoxyl)phenyl-1,3,5- s-triazine, which was synthesized from cyanuric chloride. The selective reactivity of three chlorine atoms on cyanuric chloride toward nucleophiles provides a very efficient route for the systematic synthesis of AB₂ type triazine monomers and their hyperbranched polymers. The resulting polymers exhibited a glass transition at 264°C without any indication of crystallinity. The modification of the peripheral hydroxyl groups on the hyperbranched polymers by methoxy, oligoethyleneoxy, or stearyl moieties brought about remarkable changes in their solubility and glass transition temperatures. The amphiphilic nature of the 2-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]ethoxy-terminated poly(ether ketone) analogue in an aqueous phase was investigated by using fluorescence techniques and dynamic light scattering. It was found that the analogue forms a self-aggregation at a critical aggregation concentration of 12.6 mg/L. The mean diameter of the aggregates was 320 nm. The steady-state fluorescence anisotropy value (r) of 1,6-diphenyl-1,3,5-hexatriene (DPH) in the hydrophobic domain was 0.240.