Photo- and Thermal-Induced Isomerization of Diels-Alder Adducts of Pentacene and TCNE
Abbreviated Journal Title
Eur. J. Org. Chem.
Pentacene; Isomerization; Photochemistry; Cycloaddition; Retro; -reactions; FIELD-EFFECT TRANSISTOR; THIN-FILM TRANSISTORS; PRECURSOR; ACENES; REACTIVITY; Chemistry, Organic
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.
European Journal of Organic Chemistry
"Photo- and Thermal-Induced Isomerization of Diels-Alder Adducts of Pentacene and TCNE" (2012). Faculty Bibliography 2010s. 2808.