Phase-out-compliant fluorosurfactants: unique methimazolium derivatives including room temperature ionic liquids

摘要: Expedient alkylations of 1-methyl-3H-imidazole-2-thione, a pharmaceutical active ingredient available in bulk quantities, provide high yield access to numerous protonated, or quaternized imidazoliums with chemospecific attachment the fluoroponytail at 2-mercapto functionality. The deprotonated primary target products represent valuable nitrogen heterocyclic bases, capable further substitution, and salt complex formation. Specific physicochemical characteristics that are relevant for phase surface responsive behavior, e.g. critical micelle concentration, oleophobicity, depression aqueous tension, foam formation, emulsification microgranular PTFE, investigated selected representatives compared properties common fluorosurfactants ionic liquids. Remarkably, it is found halogen bonding between iodide counterions respective polyfluoroalkylmethimazolium systems 1-iodoperfluoroalkanes, serving as σ-hole partner halides, greatly affect solubility profile resulting molecular adducts. Single-crystal X-ray structure determinations carried out across new fluorous substance classes. Strikingly, helical arrangement fluorine atoms along chains typically encountered polyfluorinated compounds not prevailing conformation. Rather, they outnumbered by structural motifs exhibiting rare zig-zag (linear alkane-like) chain Key derivatives also subjected preliminary ecotoxicological testing.