Synthesis, characterization, redox, and Hg2+ optical ion sensing properties of ferrocenyl-containing maleo- and fumaronitrile derivatives
2014
Mono-((Z)-2-amino-3-((E)-ferrocenylideneamino)butenedinitrile) (1) and bis-((E)-2,3-bis-((E)-ferrocenylideneamino)butenedinitrile) (2) substituted Schiff bases obtained by the reaction between ferrocenecarbaldehyde and diaminomaleonitrile were prepared and characterized by 1H and 13C NMR, IR, and UV-vis-NIR spectroscopy methods, elemental analysis, and X-ray crystallography. Density functional theory and time-dependent density functional theory were used to elucidate the electronic structure and the origin of observed excited states in both compounds. Electrochemical techniques were employed to investigate the possibility for the formation of a mixed-valence state of the iron centers in 2+, which are connected by a conjugated π-system. Two reversible oxidation potentials were observed in cyclic voltammetry, and spectroelectrochemical experiments revealed the presence of a low-energy intervalence charge transfer band in 2+, corresponding to class II of the mixed-valence systems. Both complexes were tested ...
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