2.2.1. Synthesis of 1st generation bromide-based IL

Bromide-based ILs (1-butyl-3-methylimidazolium bromide [Bmim][Br]) was synthesized using preexisting protocol [17]. 1-methylimidazole was reacted with 1-bromobutane in a 3-neck round bottom flask. For acetate-based ILs, similarly to [Bmim][Br], pre-existing protocol was referred to synthesize [Bmim][OAc].

[Omim][Br] was reacted with glacial acetic acid in a 3-neck round bottom flask. The 3-neck round bottom flask was then attached to a reflux condenser and refluxed for 48 h at 40 °C in neat conditions. The resulting mixture was then washed with diethyl ether and ethyl acetate. The residual solvent was removed with a rotary evaporator (Buchi Rotavapor R-300, Switzerland). NMR analysis was conducted to determine the purity of the IL. Similar synthesis route was used for the synthesis of 1-octyl-3-methylimidazolium bromide [Omim][Br], 1-dodecyl-3-methylimidazlium bromide [Domim][Br], 1- octyl-3-methylimidazolium acetate [Omim][OAc] and 1-dodecyl-3-methylimidazlium acetate [Domim][OAc]. Given the long alkyl chain of [Domim], the synthesis time was doubled from 48 h to 96 h to ensure complete reaction of starting chemicals.