Autocatalytic Synthesis of Bifluoride Ionic Liquids by SuFEx Click 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.

Ionic liquids with thioether motifs as synthetic cationic lipids for gene delivery.

This study introduces a novel class of imidazolium- and ammonium-based ionic liquids possessing two C12 and C14 tails and thioether linkers designed for lipoplex-mediated DNA delivery. Imidazolium-based ionic liquids displayed efficient gene delivery properties with low toxicity. Thiol-yne click chemistry was employed for the facile and robust synthesis of these thioether-based cationic lipioids with enhanced lipophilicity and low fluidity.