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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  Quentin Verolet  Prof Jean‐François Morin
Institution: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
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.
Keywords:density functional calculations  dyes/pigments  electrochemistry  optical properties  polycycles
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