Synthesis and ATRP of novel fluorinated aromatic monomer with pendant sulfonate group

A novel fluorinated monomer bearing sulfopropylate side group was successfully synthesized from 2,3,4,5,6-pentafluorostyrene exploiting the lability of the para-fluorine atom. The monomer was polymerized in controlled manner by aqueous atom transfer radical polymerization yielding well-defined water-soluble fluorinated aromatic polymers with pendant sulfonate groups on each repeating unit. [Display omitted] ► A fluorinated aromatic monomer with pendant sulfonate group was synthesized. ► The monomer was homopolymerized in controlled manner under aqueous ATRP conditions. ► A diblock copolymer was also obtained. ► The polymers’ thermal properties were evaluated. Novel, fluorinated monomer with pendant sulfonate group was synthesized utilizing a two-step derivatization of 2,3,4,5,6-pentafluorostyrene (FS). The first step was a nucleophilic substitution of the fluorine atom in para position by hydroxyl group followed by sulfopropylation. The monomer was polymerized under aqueous ATRP conditions to yield phenyl-fluorinated aromatic homopolymer bearing pendant sulfonates on each repeating unit. Furthermore, this polymer was used as macroinitiator for the ATRP of poly(ethylene glycol) methacrylate. The polymers were characterized by 1H NMR, SEC and FTIR analyses. Their thermal properties were evaluated by differential scanning calorimetry and thermal gravimetric analyses.