The mesomorphic properties of linear shaped homologous series based on two linkage group have been designed and synthesized with different side chain substituents (-OR) on the one end of terminal side with presence of lateral nitro group and second terminal iodo substituted group. Novel series consists thirteen members (C1 to C8, C10, C12, C14, C16, C18). Compounds (C1 to C6) showed nonliquid crystalline properties while compound (C7 to C18) displayed smectic and nematogenic mesophase properties. The textures of smectic C and nematic phase are fan, schlieren and droplets type. All these compounds were characterized by spectroscopic techniques such as [FTIR] and 1H Nuclear magnetic resonance [NMR] spectroscopy. The mesomorphic properties of these compounds were observed by POM and further confirmed by DSC and XRD. Chalconyl ester based compounds (C3 to C12) shows good antibacterial as well as antifungal activity compared with corresponding standard drugs.