The Synthesis of 1,4-bis(2-(4-(4-fluorobenzoyl)phenoxyethoxy)Benzene and poly(aralkyl ether)s Derived from 1,4-bis(2-tosyloxyethoxy)Benzene

The reaction of 1,4-bis(2-tosyloxyethoxy)benzene or 1,4-bis(bromoethoxy)-benzene with 4-fluoro-4\u27-hydroxybenzophenone was carried out under a variety of conditions. Changes were made in solvent, reaction time, work-up and base. All attempts to generate a bis(fluorobenzophenone) monomer were unsuccessful. In some cases the presence of the half-product could be determined. In other cases, an elimination product was indicated. The ditosylate, 1,4-bis(2-tosyloxyethoxy)benzene was reacted with bisphenol-A, bisphenol-AF, bis(4-hydroxyphenyl)diphenylmethane and 9,9-bis(4-hydroxyphenyl)fluorene in a dioxane - water solution in the presence of sodium hydroxide to produce four polymers. The polymers were characterized by thermal analysis (TGA) to reveal 5% weight loss temperatures of 338°, 350°, 365° and 377°, respectively. The increase in thermal stability, as judged by the 5% weight loss values, appears to be related to the aromatic content. The polymers exhibited reasonable solubility in a variety of solvents