Alkyl-templated cocrystallization of long-chain 1-bromoalkanes by lipid-like ionic liquids

The serendipitous discovery of an unorthodox ionic cocrystallization system using 2-mercaptothiazolium-based ionic liquids as a crystallization milieu paves the way for the first report of crystal structures of long-chain 1-bromoalkanes. We used single crystal X-ray diffraction to determine the structures of 1-bromo-hexadecane and 1-octadecane with the aid of ionic liquids with alkyl side chains of equivalent length to the bromoalkane at room temperature. Long alkyl chains in combination with sigma-hole interactions from strategically placed sulfur motifs synergistically function to crystallize the 1-bromoalkanes. Cocrystallization of long-chain bromoalkanes and lipid-like ionic liquids, revealing distinctive host-guest complex structures reminiscent of biomembranes.