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Autocatalytic Synthesis of Bifluoride Ionic Liquids by SuFEx Click Chemistry
Journal article   Peer reviewed

Autocatalytic Synthesis of Bifluoride Ionic Liquids by SuFEx Click Chemistry

Taha Hmissa, Xiaofei Zhang, Nilesh R Dhumal, Gregory J McManus, Xu Zhou, Hunaid B Nulwala and Arsalan Mirjafari
Angewandte Chemie (International ed.), Vol.57(49), pp.16005-16009
12-03-2018
PMID: 30112829

Abstract

autocatalysis bifluoride click chemistry ionic liquids SuFEx chemistry
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. 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).

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