title: Reduced band gap dithieno[3,2-b:2',3'-d]pyrroles: new n-type organic materials via unexpected reactivity.
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.
authors.affiliation: Division of Science and Mathematics, University of Minnesota, Morris, MN 56267, USA. pappe001@morris.umn.edu
authors.forename: Ted M
authors.initials: TM
authors.lastname: Pappenfus
authors.forename: Bethany J
authors.initials: BJ
authors.lastname: Hermanson
authors.forename: Tyler J
authors.initials: TJ
authors.lastname: Helland
authors.forename: Garett G W
authors.initials: GG
authors.lastname: Lee
authors.forename: Steven M
authors.initials: SM
authors.lastname: Drew
authors.forename: Kent R
authors.initials: KR
authors.lastname: Mann
authors.forename: Kari A
authors.initials: KA
authors.lastname: McGee
authors.forename: Seth C
authors.initials: SC
authors.lastname: Rasmussen