Synthesis and redox properties of novel ferrocenes with redox active 2,6-di-tert-butylphenol fragments: The first example of 2,6-di-tert-butylphenoxyl radicals in ferrocene system

Novel Schiff bases of ferrocenecarboxaldehyde bearing 2,6-di-tert-butyphenol fragments N-(3,5-di-tert-butyl-4-hydroxyphenyl)iminomethylferrocene (1) and N-(3,5-di-tert-butyl-4-hydroxybenzyl)iminomethylferrocene (2) have been synthesized and characterized. The oxidation of the compounds 1 and 2 by PbO2 in solution leads to the formation of stable phenoxyl radicals 1′ and 2′ studied by EPR spectroscopy. The redox properties of ferrocenes 1 and 2 were studied using cyclic voltammetry.

Graphical abstractNovel Schiff bases of ferrocenecarboxaldehyde bearing sterically hindered 2,6-di-tert-butyphenol fragments have been synthesized and characterized. The oxidation of these compounds by PbO2 in solution leads to the formation of phenoxyl radicals studied by EPR spectroscopy. The redox properties of ferrocenes with 2,6-di-tert-butylphenol and phenyl groups were studied using cyclic voltammetry.Figure optionsDownload full-size imageDownload as PowerPoint slide