Telechelic or side-functionalized diorganosiloxanes with ferrocenylimine groups

Abstract

Formyl-ferrocene, FFc, was prepared and used as agent to attach ferrocenyl moiety to siloxanes through imine group. Thus, 1,3-bis(3-aminopropyl)tetramethyldisiloxane, L1, α,ω-bis(3-aminopropyldimethylsiloxy)oligodiphenylsiloxane, L2, and poly[dimethyl-methyl(3-aminopropyl)siloxane], L3 (the last two prepared by us) were converted in the corresponding azomethine derivatives: 1,3-bis(3-ferrocenyliminepropyl)tetramethyldisiloxane, L1Fc, α,ω-bis(ferrocenyliminepropyldimethylsiloxy)oligodiphenylsiloxane, L2Fc, and poly[dimethyl-methyl(3-ferrocenyliminopropyl)siloxane], L3Fc. The iron spin state was determined by Mossbauer spectroscopy, emphasizing the presence of mixed-valence iron of interest for molecular electronics. Cyclic voltammograms of the compounds, both in solution and as films deposited on glassy carbon electrodes, showed quasi-reversible oxidation/reduction waves making them suitable for sensing applications. The solvent effect was studied by UV–Vis spectra.