Issue 6, 2006

Aryl (ferrocenyl)-capped ethenylazaferrocenes: synthesis, structure and electrochemistry

Abstract

The Horner–Wadsworth–Emmons reaction of 2,5-dimethylazaferrocene-1′-carbaldehyde with diethyl benzylphosphonate, diethyl p-methoxybenzylphosphonate and diethyl (ferrocenylmethyl)phosphonate afforded (E)-1-(2,5-dimethylazaferrocen-1′-yl)-2-phenylethene (2a), (E)-1-(2,5-dimethylazaferrocen-1′-yl)-2-(p-methoxyphenyl)ethene (2b) and (E)-1-(2,5-dimethylazaferrocen-1′-yl)-2-ferrocenylethene (2c), respectively. Cyclic voltammetry showed significant difference in the electrochemical behaviour of these compounds in comparison to their ferrocenyl counterparts. The styryl group, which is an electron-withdrawing group in the ferrocenyl compound, displays a reverse effect in the azaferrocenyl complex 2a. Introduction of the p-methoxystyryl group to 2,5-dimethylazaferrocene brings about a cathodic shift of the redox potential of 370 mV, whereas for the ferrocenyl analog the shift is only 60 mV. Compound 2c shows two redox waves due to two non-equivalent metallocenyl moieties, but there is only weak electronic coupling between redox centres. The W(CO)5-complex of 2c (4) was synthesised and its structure determined by X-ray diffraction.

Graphical abstract: Aryl (ferrocenyl)-capped ethenylazaferrocenes: synthesis, structure and electrochemistry

Supplementary files

Article information

Article type
Paper
Submitted
04 Jan 2006
Accepted
23 Mar 2006
First published
05 Apr 2006

New J. Chem., 2006,30, 901-907

Aryl (ferrocenyl)-capped ethenylazaferrocenes: synthesis, structure and electrochemistry

K. Kowalski, J. Zakrzewski, M. Palusiak and S. Domagała, New J. Chem., 2006, 30, 901 DOI: 10.1039/B600022C

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