Some newly synthesized ferrocene based esters: Characterization, DNA interaction and DFT studies

• Ferrocenyl esters have been synthesized and characterized successfully.
• DFT calculations were carried out to support the experimental data.
• Interaction with double stranded chicken blood DNA was studied by cyclic voltammetry and absorption spectroscopic methods.

A series of aromatic/aliphatic ferroceneyl-esters (E1–E10) was synthesized by condensation of 4-ferrocenyl benzoic acid (FB) with various alcohols (A1–A10). Structural elucidation of these esters was carried out by FT-IR, 1HNMR and UV–visible spectroscopic studies. Single crystal X-ray analysis was used to investigate solid state structure of E1, E4 and E8. DFT calculations were carried out at hybrid B3LYP level of theory using Density Gauss Double-Zeta with polarization functions full-electron basis sets to support the experimental data. Calculated structural parameters and FTIR vibrational frequencies of the optimized geometries were congruent to the experimental data. The interaction of the esters with double stranded chicken blood DNA was studied by cyclic voltammetry and absorption spectroscopic methods. Negative potential shift in cyclic voltammetric and the hyperchromic shift in UV–vis spectroscopy suggested external interaction (groove binding). Interaction of ferrocenyl esters with DNA were found electrostatic in nature. Free energies of ferrocenyl esters-DNA complexes indicated spontaneity of their binding.

(a) UV–Vis absorption spectra in Dichloromethane of representative ferrocenyl esters (b) UV–Vis spectra of 10 μM E4 for DNA Binding Study: (a) 0.00 μM (b) 1.1 μM (c) 2.2 μM (d) 3.3 μM (e) 4.4 μM (f) 5.5 μM at room temperature.Figure optionsDownload as PowerPoint slide