New fluorous ionic liquids function as surfactants in conventional room-temperature ionic liquids

Abstract

Ionic liquids formulated from imidazole cations with appended fluorous tails function as surfactants when added to conventional ionic liquids, facilitating the emulsification of fluoroalkanes with IL phases.

Brønsted Acidic Ionic Liquids and Their Zwitterions: Synthesis, Characterization and pKa Determination

“…[1] Low-melting ionic liquids based on imidazolium cations are the most intensively investigated among those available, and a variety of functional groups have been attached in order to modify their physical and chemical properties, including, among others, [2] amines, [3,4] amides, [4] ethers and alcohols, [5] phosphines, [6] and fluorous side chains. [7] High-melting imidazolium salts with acidic groups have been known for many years, but only recently were the first room-temperature sulfonic acid functionalized ionic liquids prepared by Davis and co-workers, who employed them as both solvent and catalyst in esterification reactions. [8] Various imidazolium cations with carboxylic ester or acid groups are known; a selection is shown in Scheme 1.…”

Ionic Liquids: Synthesis and Applications in Catalysis

“…Generally the functional groups have been introduced directly to the imidazolium moiety using the direct quaternization route. For example, imidazolium cation with hydroxyl groups [58], carboxyl groups [60], thiol groups [63], alkyne groups [64], allyl groups [65], and fluorous chains [66] were successfully prepared.…”

Aggregates in Ionic Liquids and Applications Thereof

“…More recently, premicellar aggregation in 1-butyl-3-methylimidazolium chloride and hexafluorophosphate was detected using inverse gas chromatography (Anderson et al, 2003). Merringan et al have demonstrated that imidazolium cations with long fluorous tails act as surfactants and appear to self-aggregate within imidazolium-based ILs (Merrigan et al, 2000). The possible aggregate formation by nonionic surfactants Brij-35, Brij-700, Tween-20, and Triton X-100 in emimNTf 2 was observed on the basis of the response of solvatochromic probes (Fletcher and Pandey, 2004).…”