Study of new ferrocene-based thioureas as potential nonionic surfactants

• New ferrocene based thioureas.
• Low critical micelles concentrations values.
• Electrochemical investigation.
• Experimental redox potentials correlate with DFT calculations.

Three new thiourea based ferrocenyl surfactants i.e. 1-(decanoyl)-3-(4-ferrocenylphenyl) thiourea (DP), 1-(decanoyl)-3-(4-ferrocenyl-2-methylbenzyl) thiourea (DMth), 1-(decanoyl)-3-(3-ferrocenylphenyl) thiourea (DM) have been successfully synthesized and well characterized by various analytical techniques, such as FT-IR, 1H and 13C NMR, AAS and elemental analysis. Furthermore, the single crystal XRD analysis was done for DP. To evaluate their amphiphilic nature, their CMC was determined through UV–visible spectroscopy that varies between 0.05 mM and 0.5 mM. The DP compound possesses lower CMC, whereas DM has considerably higher CMC value. Cyclic voltammetric technique was used to determine their redox behavior around CMC as well as their redox potentials, which follow the same trend as that of CMC. The DFT calculated energies of HOMO and LUMO orbitals correlate well with the experimentally determined redox potentials.

The critical micelles concentration of new ferrocenyl thioureas is evaluated by UV–visible spectroscopy defining their potential amphiphilic nature. Electrochemical studies also revealed a distinct behavior around the CMC. The experimental determined reversible redox behavior follow the same trend as predicted by DFT based energies of HOMO and LUMO orbitals.Figure optionsDownload as PowerPoint slide