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Issue 17, 2018
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Anodic electrochemistry of mono- and dinuclear aminophenylferrocene and diphenylaminoferrocene complexes

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Abstract

Two related three-membered series of nonlinear aminophenylferrocene and diphenylaminoferrocene complexes were prepared and characterized by 1H and 13C NMR spectroscopy. The first series consists of 4-(diphenylamino)phenylferrocene (TPA-Fc, 1a), its dimethoxy-substituted tetraphenylphenylenediamine derivative (M2TPPD-Fc, 1c), and the triphenylamine-bridged bis(ferrocenyl) complex (Fc-TPA-Fc, 1b). The second series involves bis(4-methoxyphenyl)aminoferrocene (M2DPA-Fc, 1d), 4-methoxyphenylaminoferrocene (MPA-Fc) with N-phenyl-appended terminal TPA (1e), and the corresponding bis(MPA-Fc) complex with bridging TPA (1f). The structure of complex 1d was further confirmed by single crystal X-ray diffraction. Combined investigations, based on anodic voltammetry, UV-vis-NIR spectroelectrochemistry and density functional theory (DFT) calculations, were conducted to illustrate the influence of the integration of multiple redox-active components on the sequential oxidation of these complexes. The first anodic steps in 1a–1f are localized preferentially on the ferrocenyl units, followed by oxidation of the TPA or TPPD moieties (absent in 1d). Irreversible oxidation of the ferrocene-appended strong donor DPA/MPA units in 1d–1f terminates the anodic series. The one-electron oxidation of the triphenylamine-bridged diferrocenyl (1b) and bis(phenylaminoferrocenyl) (1f) complexes triggers their facile redox disproportionation to dicationic bis(ferrocenium) products.

Graphical abstract: Anodic electrochemistry of mono- and dinuclear aminophenylferrocene and diphenylaminoferrocene complexes

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Publication details

The article was received on 11 Feb 2018, accepted on 10 Apr 2018 and first published on 10 Apr 2018


Article type: Paper
DOI: 10.1039/C8DT00584B
Citation: Dalton Trans., 2018,47, 6112-6123
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    Anodic electrochemistry of mono- and dinuclear aminophenylferrocene and diphenylaminoferrocene complexes

    M. Zhang, J. Zhang, J. Yin, F. Hartl and S. H. Liu, Dalton Trans., 2018, 47, 6112
    DOI: 10.1039/C8DT00584B

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