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In this paper, we report on the synthesis and application of monosubstituted diazabicyclo[2.2.2]octane (dabco) cations associated with a basic anion, dicyanamide. Key properties of these salts—phase transitions, density, and conductivity—were measured and compared to those of other common ionic liquids (ILs). Moreover, solvatochromic dyes were used to assess their solvation properties. The Heck cross-coupling reaction was evaluated in dabco-based ILs and compared with the behavior in common unfunctionalized ILs, evidencing good catalyst stability and a high recyclability in these basic ILs. [ABSTRACT FROM AUTHOR]