Research involving functionalized ionic liquids has become quite wide speared. They can serve as powerful tools to improve society, with a wide range of applications in medicine, science, and technology. As a SuFExable functionality, the sulfonyl fluoride has become widely adopted throughout the field of chemical biology due to its unique stability─reactivity pattern, highlighting the underappreciated potential of the S(VI)--F motif in ionic liquid design. For the first time, we have developed a new series of task-specific ionic liquids containing the sulfonyl fluoride motif -- a thermally stable and chemically robust functionality -- in gram-quantity scale. Significantly, inclusion of active pharmaceutical precursors and judicious variation of heterocyclic headgroups throughout the synthetic design process, resulted in structural diversity with a priori reduced ecological footprint. We employed a combination of molecular design, synthesis, computational modeling, and X-ray crystallographic studies for understanding of their structure-property relationships.