A route for the introduction of functional groups to poly(ether ether ketone) analogs, via a reactivity ratio controlled polycondensation process, has been developed. The reactivity differences, toward nucleophilic aromatic substitution reactions, of the three electrophilic sites in 3,4',5-trifluorobenzophenone, 1, affords the opportunity to prepare functionalized B-2-type monomers in situ, followed by polycondensation with the appropriate bisphenol to prepare the corresponding linear polymer. The reactivity differences in 1 were probed via a combination of C-13 and F-19 NMR spectroscopy along with model reactions using m-cresol as the nucleophile. Reaction of 1 with 1.03 molar equivalents of a series of phenols provided the desired B-2-type monomers in high selectivity. The B-2-type monomers were then converted to the linear polymers by reaction with Bisphenol-A and their structures were confirmed via NMR spectroscopy. The thermal properties were evaluated by a combination of thermogravimetric analysis and differential scanning calorimetry. (C) 2015 Elsevier Ltd. All rights reserved.