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    J Org Chem. 2008 Nov 21;73(22):8808-14. Epub 2008 Oct 15.

    Bis-morpholine-substituted perylene bisimides: impact of isomeric arrangement on electrochemical and spectroelectrochemical properties.

    Source

    School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

    Abstract

    The synthesis and separation of the 1,6- and 1,7- isomers of N,N'-bis(n-butyl)dimorpholino-3,4:9,10-perylenetetracarboxylic acid bisimide are reported. Investigations of the electrochemical and spectroscopic, in particular, spectroelectrochemical, properties of the two isomers reveal a sequence of electrochemically and chemically reversible redox processes for both isomers. Importantly, the 1,7-isomer of N,N'-bis(n-butyl)dimorpholino-3,4:9,10-perylenetetracarboxylic acid bisimide was observed to undergo a two-electron oxidation process, which contrasts with the behavior of both the corresponding 1,6-isomer and other related amino-substituted perylene bis-imide species.

    PMID:
    18855454
    [PubMed]

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