Reduced band gap dithieno[3,2-b:2',3'-d]pyrroles: new n-type organic materials via unexpected reactivity |
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Authors: | Pappenfus Ted M Hermanson Bethany J Helland Tyler J Lee Garett G W Drew Steven M Mann Kent R McGee Kari A Rasmussen Seth C |
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Affiliation: | Division of Science and Mathematics, University of Minnesota, Morris, MN 56267, USA. pappe001@morris.umn.edu |
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Abstract: | Direct addition of tetracyanoethylene to N-(p-hexylphenyl)dithieno[3,2-b:2',3'-d]pyrrole yields not only the aromatic mono- and bis-tricyanovinyl-substituted products but also a quinoidal product with dicyanomethylene groups. The analogous reaction with dithieno[3,2-b:2',3'-d]thiophene yields exclusively the aromatic mono-tricyanovinyl product. The aromatic and quinoidal products possess red-shifted absorptions, increased electron affinities, and favorable pi-stacking motifs in comparison to the unsubstituted oligomers. |
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