Methyl- and fluoro-substituted bis(4′-aminophenoxy)benzenes:: A convenient method of synthesis

We have synthesised a series of new bis(ether amine)s, primarily 1,2-bis(4'-aminophenoxy)benzene derivatives but including 1,3- and 1,4-bis(4'-aminophenoxy)benzene derivatives, with fluoro and alkyl substituents. These diamines were synthesised by fluoro displacement with 1-fluoro-4-nitrobenzene or its derivatives, or nitro displacement with 1,4-dinitrobenzene, and various phenylenediols and their alkyl- or fluoro-substituted derivatives. The resulting bis(ether nitro) compounds were reduced to the corresponding bis(ether amine)s. Thus, various bis(4'-aminophenoxy)benzenes were prepared which can be used in the synthesis of polyimides, polyamides and poly(azomethine)s with different distributions of alkyl and fluoro substituents and different substituent patterns, enabling a comprehensive study of structure-property relationships to be undertaken.