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

    Authors: contact us about adding a copy of your work at [email protected]

    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

    Share

    COinS
     

    Accessibility Statement

    This item was created or digitized prior to April 24, 2027, or is a reproduction of legacy media created before that date. It is preserved in its original, unmodified state specifically for research, reference, or historical recordkeeping. In accordance with the ADA Title II Final Rule, the University Libraries provides accessible versions of archival materials upon request. To request an accommodation for this item, please submit an accessibility request form.