Photochemical Formation of Oligothiophene Cation Radicals in Acidic Solution and Nafion

Baruch Zinger; Kent R Mann; Michael G. Hill; Larry L. Miller

doi:10.1021/cm00023a033

Photochemical Formation of Oligothiophene Cation Radicals in Acidic Solution and Nafion

Baruch Zinger, Kent R Mann, Michael G. Hill, Larry L. Miller

Chemistry (Twin Cities)

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

111 Scopus citations

Abstract

Three α-coupled terthiophenes, substituted on the terminal positions with methyl, thiomethyl, or bromo substituents, were photooxidized in a solvent mixture of methylene chloride and trifluoroacetic acid to form cation radicals. Visible, near-IR, and ESR spectra are reported. It is shown that the photooxidation requires oxygen and is acid catalyzed. In acetonitrile/trifluoroacetic acid, cation radical π-dimers are formed. Using Nafion, stable films of the cation radical dimer or dication of 2, 5ʺ-bis(thiomethyl)terthiophene could be formed.

Original language	English (US)
Pages (from-to)	1113-1118
Number of pages	6
Journal	Chemistry of Materials
Volume	4
Issue number	5
DOIs	https://doi.org/10.1021/cm00023a033
State	Published - Feb 1 1992

Access

10.1021/cm00023a033

Fingerprint Dive into the research topics of 'Photochemical Formation of Oligothiophene Cation Radicals in Acidic Solution and Nafion'. Together they form a unique fingerprint.

Cite this

@article{f36e912d94b344c3b61cccd5629b8fcb,

title = "Photochemical Formation of Oligothiophene Cation Radicals in Acidic Solution and Nafion",

abstract = "Three α-coupled terthiophenes, substituted on the terminal positions with methyl, thiomethyl, or bromo substituents, were photooxidized in a solvent mixture of methylene chloride and trifluoroacetic acid to form cation radicals. Visible, near-IR, and ESR spectra are reported. It is shown that the photooxidation requires oxygen and is acid catalyzed. In acetonitrile/trifluoroacetic acid, cation radical π-dimers are formed. Using Nafion, stable films of the cation radical dimer or dication of 2, 5ʺ-bis(thiomethyl)terthiophene could be formed.",

author = "Baruch Zinger and Mann, {Kent R} and Hill, {Michael G.} and Miller, {Larry L.}",

year = "1992",

month = feb,

day = "1",

doi = "10.1021/cm00023a033",

language = "English (US)",

volume = "4",

pages = "1113--1118",

journal = "Chemistry of Materials",

issn = "0897-4756",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Photochemical Formation of Oligothiophene Cation Radicals in Acidic Solution and Nafion

AU - Zinger, Baruch

AU - Mann, Kent R

AU - Hill, Michael G.

AU - Miller, Larry L.

PY - 1992/2/1

Y1 - 1992/2/1

N2 - Three α-coupled terthiophenes, substituted on the terminal positions with methyl, thiomethyl, or bromo substituents, were photooxidized in a solvent mixture of methylene chloride and trifluoroacetic acid to form cation radicals. Visible, near-IR, and ESR spectra are reported. It is shown that the photooxidation requires oxygen and is acid catalyzed. In acetonitrile/trifluoroacetic acid, cation radical π-dimers are formed. Using Nafion, stable films of the cation radical dimer or dication of 2, 5ʺ-bis(thiomethyl)terthiophene could be formed.

AB - Three α-coupled terthiophenes, substituted on the terminal positions with methyl, thiomethyl, or bromo substituents, were photooxidized in a solvent mixture of methylene chloride and trifluoroacetic acid to form cation radicals. Visible, near-IR, and ESR spectra are reported. It is shown that the photooxidation requires oxygen and is acid catalyzed. In acetonitrile/trifluoroacetic acid, cation radical π-dimers are formed. Using Nafion, stable films of the cation radical dimer or dication of 2, 5ʺ-bis(thiomethyl)terthiophene could be formed.

UR - http://www.scopus.com/inward/record.url?scp=0000084765&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000084765&partnerID=8YFLogxK

U2 - 10.1021/cm00023a033

DO - 10.1021/cm00023a033

M3 - Article

AN - SCOPUS:0000084765

VL - 4

SP - 1113

EP - 1118

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 5

ER -

Photochemical Formation of Oligothiophene Cation Radicals in Acidic Solution and Nafion

Abstract

Access

Other files and links

Cite this