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

doi:10.1021/ol8002018

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

60 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 language	English (US)
Pages (from-to)	1553-1556
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	8
DOIs	https://doi.org/10.1021/ol8002018
State	Published - Apr 17 2008

Access

10.1021/ol8002018

OpenUrl availability

Full text

Cite this

@article{204130c39c2c44db93743ad2125583bd,

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 W-(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 π stacking motifs in comparison to the unsubstituted oligomers.",

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

year = "2008",

month = apr,

day = "17",

doi = "10.1021/ol8002018",

language = "English (US)",

volume = "10",

pages = "1553--1556",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Reduced band gap dithieno[3,2-b:2',3',-d]pyrroles

T2 - New n-type organic materials via unexpected reactivity

AU - Pappenfus, Ted M.

AU - Hermanson, Bethany J.

AU - Helland, Tyler J.

AU - Lee, Garett G.W.

AU - Drew, Steven M.

AU - Mann, Kent R

AU - McGee, Kari A.

AU - Rasmussen, Seth C.

PY - 2008/4/17

Y1 - 2008/4/17

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=58149199529&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=58149199529&partnerID=8YFLogxK

U2 - 10.1021/ol8002018

DO - 10.1021/ol8002018

M3 - Article

C2 - 18348567

AN - SCOPUS:58149199529

SN - 1523-7060

VL - 10

SP - 1553

EP - 1556

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

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

Abstract

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this