In present strudy, the synthesis and characterization of monocationic 1,3-tetradecylimidazolium;
[(C14)2Im]Br and tricationic benzene centered tris-tetradecyl/hexadecyl imidazolium bromide salts; i.e.
[(C14)3C6H3Im]Br3 and [(C16)3C6H3ImBr]Br3 is reported. The stabilizer role of imidazolium salts to prepare
silver nanoparticles (AgNPs) via chemical reduction method was investigated. To understand the reaction
medium effect on the size and morphology control of AgNPs, monophasic (aqueous medium) and biphasic
(DCM/H2O) approaches were applied. The morphology control was noticed for AgNPs protected with
[(C14)3C6H3Im]Br3 (show sphere like morphology) and [(C14)2Im]Br (show dendritic structures) via
biphasic approach. A clear variation in the size and morphology of AgNPs was noticed by varying the
type of stabilizers and reaction medium. It was also observed that AgNPs were formed and stabilized
only in aqueous medium in both approaches, thus it is assumed that AgNPs surfaces were protected by
imidazolium salts with bilayer fashion. Anticancer activity of imidazolium salts was performed by
MTT assay against HeLa cancer cell lines. The result shows that cytotoxic activity of tricationic
[(C14)3C6H3Im]Br3 was more potent than that of monocationic [(C14)2Im]Br. The outcome suggests
that there is an urgent need to develop new polycationic imidazolium salts for various chemical and
medicinal applications.