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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Synthesis, crystal structures and electrochemical properties of ferrocenyl imidazole derivatives
Ayomide H Labulo1, Bernard Omondi1, Vincent O Nyamori1
1School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, South Africa.
Abstract:
Six ferrocenyl imidazole derivatives substituted with -Cl, -NO2 and -CH3 on the 2-position of the 1H-imidazole ring have been synthesized. Of the six compounds, the di-substituted ferrocenes, i.e. compounds 4 (1,1'-ferrocenylmethyl(2-chloroimidazole)), 5 (1,1'-ferrocenyl(2-nitroimidazole)), and 6 (1,1'-ferrocenylmethyl(2-methylimidazole)) are reported for the first time. The structure-property relationships of compounds 4, 5 and 6 were investigated by means of UV-visible, FTIR, 1H-NMR, 13C-NMR spectroscopy and electrochemical studies. UV-visible analysis in acetonitrile showed that the π -π* band of compounds 2 (1-ferrocenylmethyl(2-nitroimidazole)) and 5 appeared at longer wavelength compared to 1 (1-ferrocenylmethyl(2-chloroimidazole)), 3 (1-ferrocenylmethyl(2-methylimidazole)), 4 and 6. This phenomenon is due to the different electronics around the imidazole moieties. In cyclic voltammetry analysis, all compounds exhibited a quasi-reversible redox wave for the ferrocenyl and imidazole moieties. Density functional theoretical (DFT) calculations with the B3LYP/6-311+G(d) basis set were performed on compounds 1-6, and the calculated HUMO-LUMO band gap energies correlated with those obtained from electrochemical and spectroscopic data. The X-ray crystallographic analysis highlighted the effect of electron-withdrawing and electron-donating substituents on the conformation of the cyclopentadienyl rings attached to the ferrocenyl moiety.
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