Reduced band gap dithieno[3,2-b:2',3',-d]pyrroles: New n-type organic materials via unexpected reactivity

Ted M. Pappenfus, Bethany J. Hermanson, Tyler J. Helland, Garett G.W. Lee, Steven M. Drew, Kent R Mann, Kari A. McGee, Seth C. Rasmussen

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Direct addition of tetracyanoethylene to W-(p-hexylphenyl)dithieno[3,2-b: 2́,3́-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:2́, 3́-d]thiophene yields exclusively the aromatic mono-tricyanovinyl product. The aromatic and quinoidal products possess red-shifted absorptions, increased electron affinities, and favorable π stacking motifs in comparison to the unsubstituted oligomers.

Original languageEnglish (US)
Pages (from-to)1553-1556
Number of pages4
JournalOrganic Letters
Volume10
Issue number8
DOIs
StatePublished - Apr 17 2008

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