Functional macrocyclic polysulfones via aminomethylpolysulfone

Amidoalkylation of polysulfone (PS) with N‐chloromethylphthalimide (CMPi) to polymer 2/2a (PiPs), followed by hydrazinolysis of PiPs in CHCl3 with neat N2H4 + H2O (RT 3 days) to aminomethylpolysulfone (3, AMPS). Condensation of AMPS with 4‐chlorosulfonylbenzo‐18‐crown‐6 produced B18C6AMPS. Okawara‐type condensations with diglycydyl glycols (5) led to azacrown polysulfone polymers 6d, and polystyrene azacrown polymers 6a–6c. Products were characterized by 270 MHz 1H‐NMR, thermogravimetric (TGA) and DSC analysis. Insoluble aminomethylpolystyrene beads were used as model supports to study the Okawara‐type reaction with diglycydyl ethers and the products showed thermoregulated complexation of alkali salts on polymers 6b and 6c. Polysulfone membranes were prepared from B18C6AMPS and transport of K+ in a liquid membrane‐type experiment was demonstrated.