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Autocatalytic Synthesis of Bifluoride Ionic Liquids by SuFEx Click Chemistry
Author(s) -
Hmissa Taha,
Zhang Xiaofei,
Dhumal Nilesh R.,
McManus Gregory J.,
Zhou Xu,
Nulwala Hunaid B.,
Mirjafari Arsalan
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808304
Subject(s) - chemistry , ionic liquid , electrochemistry , autocatalysis , ionic bonding , alkyl , inorganic chemistry , ionic conductivity , combinatorial chemistry , ion , organic chemistry , electrode , catalysis , electrolyte
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.