Autocatalytic Synthesis of Bifluoride Ionic Liquids by SuFEx Click Chemistry. Issue 49 (3rd September 2018)

• Record Type: Journal Article
• Authors: Hmissa, Taha; Zhang, Xiaofei; Dhumal, Nilesh R.; McManus, Gregory J.; Zhou, Xu; Nulwala, Hunaid B.; Mirjafari, Arsalan
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 49(2018)
• Page Start: 16005
• Page End: 16009
• Publication Date: 2018-09-03
• Subjects: autocatalysis -- bifluoride -- click chemistry -- ionic liquids -- SuFEx chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808304
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Ionic liquids with bifluoride anions possess properties such as high conductivity, wide electrochemical windows, and low viscosity that make them attractive materials for various electrochemical devices. However, owing to the lack of reliable synthetic routes, bifluoride‐based ionic liquids have seldom been explored. Herein, an autocatalytic strategy for the HF‐free synthesis of bifluoride‐based sulfonamide ionic liquids based on the sulfur(VI) fluoride exchange (SuFEx) reaction is reported. This reaction requires no chromatographic purification, and yields are quantitative. The thermophysical properties (phase transition behavior and decomposition temperature) and electrochemical stabilities of the resulting products were studied. The products with alkyl, aryl, and perfluoroalkyl side chains exhibited extraordinarily wide electrochemical windows (up to 6.0 V) with reproducible results among multiple replicate measurements. Abstract : An autocatalytic strategy for the HF‐free synthesis of bifluoride‐based sulfonamide ionic liquids that is enabled by the sulfur(VI) fluoride exchange (SuFEx) reaction requires no chromatographic purification, and yields are quantitative. The resulting products with alkyl, aryl, and perfluoroalkyl side chains exhibit very wide electrochemical windows (up to 6.0 V).