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

Chem Sci. 2024 Oct 22. doi: 10.1039/d4sc05422a. Online ahead of print.

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.