SYNTHESIS OF AROMATIC POLYETHERS BY SCHOLL REACTION .5. SYNTHESIS AND POLYMERIZATION OF 1,3-BIS[4-(1-NAPHTHOXY)BENZOYL]BENZENE, 1,4-BIS[4-(1-NAPHTHOXY)BENZOYL]BENZENE, BIS[4-(1-NAPHTHOXY)PHENYL]METHANE, 1,3-BIS[4-(1-NAPHTHOXY)PHENYLMETHYL]BENZENE, AND 1,4-BIS-[4-(1-NAPHTHOXY)PHENYLMETHYL]BENZENE

This article describes the synthesis and the cation-radical polymerization (Scholl reaction) of 1,3-bis[4-(1-naphthoxy)benzoyl]benzene (6) and 1,4-bis[4-(1-naphthoxy)benzoyl]benzene (7) initiated by FeCl3. This polymerization produced poly(ether ether ketone ketone)s (PEEKK) of number average molecular weight (MBARn) up to 5400 g/mol. The synthesis of bis[4-(1-naphthoxy)phenyl]methane (8), 1,3-bis[4-(1-naphthoxy)phenylmethyl]benzene (9), and 1,4-bis[4-(1-naphthoxy)phenylmethyl]benzene (10) are also described. Polyethers of MBARn up to 15400 g/mol at a FeCl3/monomer molar ratio of 2/1 were obtained. An increased polymerizability of the monomers 9 and 10 containing two CH2 groups versus that of the corresponding monomers containing two carbonyl groups (6 and 7) was observed. This enhanced polymerizability was explained based on the increased nucleophilicity of the monomers 9 and 10.