Nicotine-based surface active ionic liquids: Synthesis, self-assembly and cytotoxicity studies

Abstract

New ester-functionalized surface active ionic liquids (SAILs) based on nicotine, [CnENic][Br] (n=8, 10 and 12), with bromide counterions have been synthesized, characterized and investigated for their self-assembly behavior in aqueous medium. Conductivity measurements in aqueous solutions of the investigated SAILs have provided information about their critical micelle concentration (cmc), and degree of counterion binding (β), where cmc was found to be 2–3-fold lower than homologous SAILs or conventional cationic surfactants. The inherent fluorescence of SAILs in the absence of any external fluorescent probe have shed light on cmc as well as interactions prevailing between the monomers in micelle at molecular level. The thermodynamic parameters related to micellization have been deduced from isothermal titration calorimetry (ITC) and conductivity measurements. 1H NMR, spin-lattice (T1) relaxation time and 2D 1H-IH ROESY measurements have been exploited to get detailed account of internal structure of micelle. The size and shape of the micelles have been explored using dynamic light scattering (DLS) and transmission electron microscopy (TEM) measurements. The synthesized SAILs have been found to be non-cytotoxic towards C6-Glioma cell line, which adds to the possible utility of these SAILs for diverse biological applications.