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Issue 9, 2002
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Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres

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Abstract

The mixed-valence character of four bis(N,N-dihydrodimethylphenazine) radical cation derivatives with varying π-electron bridges was investigated. The electron transfer (ET) distance within these derivatives varies from ca. 12.5 Å for 1,2-bis[2-(5,10-dihydro-5,10-dimethylphenazinyl)]acetylene (1) to ca. 19.3 Å for 9,10-bis[2-(5,10-dihydro-5,10-dimethylphenazinyl)ethynyl]anthracene (4). All radical cation species show intense intervalence charge-transfer (IV-CT) bands in the NIR. The Mulliken–Hush analysis was used to derive the electronic coupling V, which ranges from 310 to 870 cm−1. Comparisons with analogous ET systems in which the dihydrodimethylphenazine redox centres have been replaced by triarylamine units show that the dihydrodimethylphenazine species have a significantly higher internal reorganisation energy associated with the ET. This behaviour is attributed to C–N stretching and C–C ring modes of the dihydrodimethylphenazine units.

Graphical abstract: Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres

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Publication details

The article was received on 08 May 2002, accepted on 09 Jul 2002 and first published on 06 Aug 2002


Article type: Paper
DOI: 10.1039/B204392K
J. Chem. Soc., Perkin Trans. 2, 2002, 1553-1561

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    Organic mixed valence compounds with N,N-dihydrodimethylphenazine redox centres

    M. Holzapfel, C. Lambert, C. Selinka and D. Stalke, J. Chem. Soc., Perkin Trans. 2, 2002, 1553
    DOI: 10.1039/B204392K

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