Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors

S. Van Mierloo, K. Vasseur, N. Van Den Brande, A.E. Boyukbayram, B. Ruttens, S.D. Rodriguez, E. Botek, V. Liégeois, J. D'Haen, P.J. Adriaensens, P. Heremans, B. Champagne, G. Van Assche, L. Lutsen, D.J. Vanderzande, W. Maes

Research output: Contribution to journalArticle

Abstract

A series of 5′-aryl-substituted 2, 5-bis(3′-hexylthiophen- 2′-yl)thiazolo[5, 4-d]thiazole derivatives was synthesized and these expanded semiconductors were investigated as active materials for solution-processable organic field-effect transistors. Field-effect mobilities of up to 10 cm V s were obtained, representing the first reasonable FET behavior for highly soluble thiazolo[5, 4-d]thiazole-based small organic compounds suitable for printable electronics. Thermal and electrooptical material properties were studied by thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and UV/Vis spectroscopy. Trends in thermal and optical data were supported by (time-dependent) density functional theory calculations. Additional X-ray diffraction, atomic force microscopy, and scanning electron microscopy studies provided insight in the relationship between the molecular structures, film morphologies, and FET performances. The fibrillar microcrystalline structure observed for the best-performing thienyl-substituted material was linked to the high mobility.
Original languageEnglish
Pages (from-to)923-930
Number of pages8
JournalChemPlusChem
Volume77
Issue number10
DOIs
Publication statusPublished - 1 Oct 2012

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    PAI n°P7/05 - FS2: Functional Supramolecular Systems (FS2)

    CHAMPAGNE, B., De Vos, D., Van der Auweraer, M., Jérôme, C., Lazzaroni, R., Marin, G., Jonas, A., Du Prez, F., Vanderzande, D., Van Tendeloo, G., Van Speybroeck, V., NENON, S. & STAELENS, N.

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    Functional Supramolecular Systems (PAI P6/27)

    CHAMPAGNE, B., WOUTERS, J., BOTEK, E., DE WERGIFOSSE, M., GUTHMULLER, J., Liegeois, V., NORBERG, B., Plaquet, A., STAELENS, N. & Vercauteren, D.

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  • Cite this

    Van Mierloo, S., Vasseur, K., Van Den Brande, N., Boyukbayram, A. E., Ruttens, B., Rodriguez, S. D., Botek, E., Liégeois, V., D'Haen, J., Adriaensens, P. J., Heremans, P., Champagne, B., Van Assche, G., Lutsen, L., Vanderzande, D. J., & Maes, W. (2012). Functionalized dithienylthiazolo[5, 4-d]thiazoles for solution-processable organic field-effect transistors. ChemPlusChem, 77(10), 923-930. https://doi.org/10.1002/cplu.201200132