Combined experimental and theoretical study of the novel ferrocene derivatives and examining the effect of E-Z stereoisomerism on their optical properties
OPTICAL MATERIALS, cilt.89, ss.452-459, 2019 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 89
- Basım Tarihi: 2019
- Doi Numarası: 10.1016/j.optmat.2019.01.072
- Dergi Adı: OPTICAL MATERIALS
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.452-459
- Anahtar Kelimeler: Ferrocene derivatives, E-Z stereoisomerism, Film coating, Optical conductivity, DFT, CONFORMATIONAL-ANALYSIS, THIN-FILMS, SPECTROSCOPY, CHEMISTRY, POLYMER, ACIDS
- Van Yüzüncü Yıl Üniversitesi Adresli: Hayır
Özet
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.