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Bis-morpholine-Substituted Perylene Bisimides: Impact of Isomeric Arrangement on Electrochemical and Spectroelectrochemical Properties

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    Bis-morpholine-Substituted Perylene Bisimides: Impact of Isomeric Arrangement on Electrochemical and Spectroelectrochemical Properties
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    School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, U.K., and Daresbury Laboratory, Synchrotron Radiation Source, Warrington, WA4 4AD Cheshire, England
    [email protected]
    †University of Nottingham.
    ‡Synchrotron Radiation Source.
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2008, 73, 22, 8808–8814
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    https://doi.org/10.1021/jo801557e
    Published October 15, 2008
    Copyright © 2008 American Chemical Society
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    Abstract

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    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.

    Copyright © 2008 American Chemical Society

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    Supporting Information

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    Full experimental details, original 1H and 13C NMR spectra, and mass spectra for 1a and 1b; full UV−vis and EPR data for all the oxidation and reduction processes; further details of DFT calculations. Details of structural refinement and CIF file for 1b. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    This article is cited by 32 publications.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2008, 73, 22, 8808–8814
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo801557e
    Published October 15, 2008
    Copyright © 2008 American Chemical Society
    Request reuse permissions

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