A series of functionalised imidazolium halide salts with substituents able to form pi-bonds have been prepared and characterised. Subsequent reaction of these imidazolium halides with Ag[C(CN)(3)] affords imidazolium-based ionic liquids (ILs), some of which are characterised by extensive pi-pi interactions between the cation and [C(CN)(3)] anion. The conductivities of the room temperature ILs with the [C(CN)(3)] anion were determined and the IL with an alkene functionality exhibits the highest conductivity, exceeding that of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, a commonly used IL electrolyte. No clear correlations between the extent of pi-pi interactions and the conductivities were observed.