Ferrocene- and ruthenocene-containing chalcones: A spectroscopic and electrochemical study

Chalcones of the type Mc-CO–CHCH-Ph, Ph-CO–CHCH-Mc and Mc-CO–CHCH-Mc with Mc = Fc = ferrocenyl or Rc = ruthenocenyl, and Ph = phenyl were synthesized. Synthesis was achieved by base catalyzed Claisen–Schmidt condensation of the appropriated acetyl and aldehyde in ethanol. Cyclic voltammetry in CH3CN in the presence of 0.1 mol dm−3 [N(Bu)4][PF6] revealed chemical and electrochemical reversible behaviour for the Fc/Fc+ couple and irreversible electrochemistry for the two electron Rc/Rc2+ couple. The potential ranges for the Fc/Fc+ couple varied in the range 138 ⩽ E°′ ⩽ 302 mV while Epa for Rc/Rc2+ couple was between 358 and 510 mV vs. FcH/FcH+, the internal standard. Chalcones with the carbonyl group adjacent to the metallocene, are more difficult to oxidize.

A variety of ferrocene- and/or ruthenocene-containing chalcones were synthesized by reacting the appropriated acetyl and aldehyde under basic conditions. Electrochemistry of these complexes revealed chemical and electrochemical reversibility for the Fc/Fc+ couple and irreversible electrochemistry for the Rc/Rc2+ couple.Figure optionsDownload as PowerPoint slideHighlights
► A variety of ferrocene- and/or ruthenocene-containing chalcones were synthesized.
► Electrochemistry gave reversible Fc/Fc+ couples in CH3CN/0.1 mol dm−3 [NBu4][PF6].
► Irreversible electrochemical behaviour was obtained for the Rc/Rc2+ couples.
► Rc2+ is inclined to undergo conversions to regain an 18-electron configuration.