Installation of superacidic carbon acid moieties into polymer materials via post-polymerization modification

Abstract

In the fields of polymer and material chemistries, strong acid units have mainly included sulfonic acids, which has limited the extension of related material chemistries. Here, a unique carbon acid functionality, namely the bis[(trifluoromethyl)sulfonyl]methyl group, was integrated with polymers via a simple postpolymerization modification with the outstandingly electrophilic 1,1-bis[(trifluoromethyl)sulfonyl]ethylene. The proposed synthesis protocol was verified as an efficient process even for solid-state reactions. The synthesis afforded an organic material with a surface decorated with bis[(trifluoromethyl)sulfonyl]methyl units. The fabricated membranes featuring surface bis[(trifluoromethyl)sulfonyl]methyl units functioned as efficient organocatalysts with high catalytic activity for the Mukaiyama aldol reaction. This study provides a simple method for installing superacidic carbon acid moieties onto the surfaces of materials without tedious chemical treatments.