Aromatic polyethers: Syntheses, mechanisms of formation, characterization and properties

Aromatic polyether ketones were synthesized by the reaction of 1,3-bis(chlorobenzoyl)benzene (1,3-CBB) or the corresponding fluoro analog (1,3-FBB) with bisphenoxides derived from either bisphenol-A or hydroquinone in DMAc/toluene. With the stronger nucleophile, obtained from bisphenol-A, and either of the halides, high molecular weight polymers are formed exclusively via a nucleophilic aromatic substitution (S;The effects of N-methylpyrrolidinone (NMP) as a solvent on the polymerization reactions of 1,3-CBB and 1,3-FBB with bisphenol-A were examined. Anhydrous potassium carbonate was used as the base. High molecular weight polymers could not be obtained from 1,3-CBB due to dehalogenation of 1,3-CBB via S;Competing reactions were also observed when either dihaloazo or azoxybenzene derivatives were allowed to react with various bisphenoxides in NMP. Photo-induced viscosity change with azoaromatic polyethers due to cis-trans isomerization were investigated. Photochemical rearrangement of the aromatic azoxy containing polyethers to hydroxyazo containing polymers were studied. Both, azo and azoxyaromatic polyethers undergo crosslinking at elevated temperatures.