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4,10-Dibromoanthanthrone as a New Building Block for p-Type, n-Type, and Ambipolar π-Conjugated Materials

Authors

  • Jean-Benoît Giguère,

    1. Département de Chimie et Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, Pavillon A.-Vachon, 1045 Ave de la Médecine, Québec, G1V 0A6 (Canada), Fax: (+1) 418-656-7916
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  • Quentin Verolet,

    1. Département de Chimie et Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, Pavillon A.-Vachon, 1045 Ave de la Médecine, Québec, G1V 0A6 (Canada), Fax: (+1) 418-656-7916
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  • Prof. Jean-François Morin

    Corresponding author
    1. Département de Chimie et Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, Pavillon A.-Vachon, 1045 Ave de la Médecine, Québec, G1V 0A6 (Canada), Fax: (+1) 418-656-7916
    • Département de Chimie et Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, Pavillon A.-Vachon, 1045 Ave de la Médecine, Québec, G1V 0A6 (Canada), Fax: (+1) 418-656-7916
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Abstract

New p-type, n-type, and ambipolar molecules were synthesized from commercially available 4,10-dibromoanthanthrone dye. Substitution at the 4,10- and 6,12-positions with different electron-rich and electron-poor units allowed the modulation of the optoelectronic properties of the molecules. A bis(dicyanovinylene)-functionalized compound was also prepared with a reduction potential as low as −50 mV versus Ag+ with a crystalline two-dimensional lamellar packing arrangement. These characteristics are important prerequisites for air-stable n-type organic field-effect transistor applications.

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