Synthesis and proton conductivities of phosphonic acid containing poly-(arylene ether)s

A novel phosphonic acid containing bisphenol was successfully synthesized from phenolphthalein and m-aminophenylphosphonic acid. A series of homo- and copoly-(arylene ether)s containing phosphonic acid groups were prepared by solution nucleophilic polycondensation. These phosphonic acid containing polymers can readily be dissolved in common organic solvents, such as dimethyl sulfoxide, N-methyl-2-pyrrolidinone, and N-cyclohexylpyrrolidinone, and can be cast into tough and smooth films. The presence of phosphonic acid pendants in the poly-(arylene ether)s was confirmed by NMR, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and conductivity measurements. This is the first report on the attachment of phenylphosphonic acid groups as side chains to aromatic polyethers. These poly-(arylene ether)s had very high glass-transition temperatures ranging from 254 to >315°C and high molecular weights. The conductivities of the synthesized polymers were analyzed by the Cole-Cole method, and they ranged from 10^-5 to 10^-6 Scm^-1. The synthesized polymers also exhibited good solution processability.