Combined experimental and theoretical study of the novel ferrocene derivatives and examining the effect of E-Z stereoisomerism on their optical properties

Herein, we present the primary results on two valuable E-Z stereoisomers containing ferrocene scaffold [(E)-5,5-dimethy1-3-oxo-2-(2-phenyl-2-ferrocenyl-vinyl)cyclohex-1-en-1-yl acetate (E-FerCycAc) and its Z-stereoisomer (Z-FerCycAc)]. These compounds were both prepared from 1-phenylvinyl-ferrocene and 5,5-dimethyl-1,3-cyclohexanedione under catalysis of manganese(III) acetate according to the radical addition mechanism. The prominent spectroscopic data of the target stereoisomers were provided by FT-IR, LC-MS, (1) H NMR, (13) C NMR techniques, and their stereochemical identification was made primarily by NOESY analysis. The corresponding data (absorbance, transmittance and optical and transport energy gap) were collected from UV-vis studies. The optical properties of the glass slides coated with E-FerCycAc and Z-FerCycAc films were examined and consequently, the optical and transport energy band gap values of the E-FerCycAc were found significantly lower than Z-FerCycAc. The physicochemical and spectroscopic findings (HOMO-LUMO energies, bandgap values, UV-vis, FT-IR, (1) H, and (13) C NMR spectra) were also compared and supported with the acquired DFT calculations.