Photo- and Thermal-Induced Isomerization of Diels-Alder Adducts of Pentacene and TCNE

    Authors

    V. K. Johns; Z. Shi; W. F. Hu; J. B. Johns; S. L. Zou;Y. Liao

    Comments

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    Abbreviated Journal Title

    Eur. J. Org. Chem.

    Keywords

    Pentacene; Isomerization; Photochemistry; Cycloaddition; Retro; -reactions; FIELD-EFFECT TRANSISTOR; THIN-FILM TRANSISTORS; PRECURSOR; ACENES; REACTIVITY; Chemistry, Organic

    Abstract

    Herein we report the formation of the second-ring DielsAlder adduct together with the central-ring adduct in a reaction of pentacene and tetracyanoethylene at room temperature. DFT calculations showed that the difference between the free energy of the two isomers is about 3.9 kcal/mol. Photo- and thermal-induced isomerization between the central-ring adduct and the second-ring adduct were studied in solution and in polymer films. In solution, the less-stable second-ring adduct can be converted into the more-stable central-ring adduct either thermally or photochemically, but the reverse transformation does not occur. In a polymer matrix, isomerization can be photochemically induced in both directions at different wavelengths, which results in a photoswitchable system. Formation of pentacene in the photochemical experiments was also observed, which supports an isomerization process involving a photo-retro-DielsAlder reaction.

    Journal Title

    European Journal of Organic Chemistry

    Issue/Number

    14

    Publication Date

    1-1-2012

    Document Type

    Article

    Language

    English

    First Page

    2707

    Last Page

    2710

    WOS Identifier

    WOS:000303440000003

    ISSN

    1434-193X

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