Synthesis and Physical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs)

Abstract

Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has been developed. Herein, a wide variety of those ionic liquids (ILs) is presented in terms of their cation structure. The authors synthesized ILs containing the bromide or bis(trifluoromethane)sulfonimide anion and 1-aryl-3-alkyl imidazolium cations with various substituents in the ortho and/ or para position of the phenyl ring and alkyl chains of different lengths varying from butyl to dodecyl. The differences of their physical properties (melting point, thermal decomposition, viscosity, electro-chemical window) of these ILs are reported according to their structure.

Understanding the Reaction Kinetics and Microdynamics between Methylimidazole and Alkyl Thiocyanate for Ionic Liquid Synthesis through Experiments and Theoretical Calculation

“…Ionic liquids (ILs), composed exclusively of ions, have considerable applications in the fields such as catalysis, , extraction, and separation due to their negligible vapor pressure, high ionic conductivity, large temperature stability, and good solvent properties. − For a given application, the properties of ILs can be easily tuned by different cations and anions. , In particular, the alkyl chain length of cations plays an important role in the properties of ILs, including density, conductivity, surface tension, and diffusion coefficient. , However, the synthesis of ILs with a long alkyl chain usually takes a very long reaction time . For example, the reaction of aniline derivatives with a long alkyl chain requires a long time of 2–7 days at 70 °C without reaction kinetics parameters …”

Friedel–Crafts acylation of benzene derivatives in tunable aryl alkyl ionic liquids (TAAILs)

“…TAAILs 1 – 6 are then formed by an anion exchange reaction using lithium bis(trifluoromethylsulfonyl)imide (LiNTf 2 ). All reactions are generally tolerant towards different aryl substitutions, substitution patterns, alkyl chain lengths and can be carried out in a multigram scale [ 57 ].…”

“…TAAILs 1-6 are then formed by an anion exchange reaction using lithium bis(trifluoromethylsulfonyl)imide (LiNTf 2 ). All reactions are generally tolerant towards different aryl substitutions, substitution patterns, alkyl chain lengths and can be carried out in a multigram scale [57]. The acylation of the electron-rich benzene derivative anisole with acetic anhydride (Ac 2 O) to acetanisole 7 was chosen as the model reaction (Scheme 2) [36].…”

The Facile Deposition of Pt Nanoparticles on Reduced Graphite Oxide in Tunable Aryl Alkyl Ionic Liquids for ORR Catalysts

“…The synthesis and characterization of the TAAILs used here were described elsewhere [ 15 , 29 , 30 ]. TAAILs refer to 1-n-alkyl-3-arylimidazolium ILs ( Scheme 1 ).…”

“…The TAAILs can be obtained on a large gram scale, and the synthesis allows manifold variations of the aryl and alkyl groups [ 15 , 29 , 30 ]. The anion purity of the TAAILs was characterized via ion chromatography and has always been found above at least 97% and more often 99%.…”