Donor-acceptor conjugated polymers based on p- and o-benzodifuranone and thiophene derivatives: electrochemical preparation and optical and electronic properties

Kai Zhang, Bernd Tieke, John C. Forgie, Filipe Vilela, Peter J. Skabara

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A series of pi-conjugated polymers consisting of bis-EDOT or bis-EDTT units and p- or o-diphenylbenzodifuranones have been prepared electrochemically. The monomers and polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. The monomers were synthesized from 3,4-ethylenedioxythien-2-yl or 3,4-ethylenedithiathien-2-yl trimethylstannane and 3,7-bis(4-bromophenyl)benzo[1,2-b:4,5-b']difuran-2,6-dione or 3,6-bis(4-bromophenyl)benzo[1,2-b:6,5-b']difuran-2,7-dione using Stile coupling. The polymers exhibit broad absorption bands, and strong donor-acceptor characteristics with very small band gaps (in a range from 0.40 to 1.20 eV). Electrochemically grown polymer thin films exhibit reversible behavior under oxidative and reductive conditions. Under reduction, the polymer films show color changes from dark to almost transparent.

LanguageEnglish
Pages743-750
Number of pages8
JournalMacromolecules
Volume45
Issue number2
DOIs
Publication statusPublished - 24 Jan 2012

Fingerprint

Thiophenes
Conjugated polymers
Thiophene
Polymer films
Electronic properties
Polymers
Optical properties
Monomers
Derivatives
Ultraviolet spectroscopy
Absorption spectroscopy
Cyclic voltammetry
Absorption spectra
Energy gap
Color
Thin films
trimethyltin

Keywords

  • monomers
  • conjugated polymers
  • o-benzodifuranone
  • thiophene derivatives

Cite this

Zhang, Kai ; Tieke, Bernd ; Forgie, John C. ; Vilela, Filipe ; Skabara, Peter J. / Donor-acceptor conjugated polymers based on p- and o-benzodifuranone and thiophene derivatives : electrochemical preparation and optical and electronic properties. In: Macromolecules. 2012 ; Vol. 45, No. 2. pp. 743-750.
@article{bdaa3caaef01499ca93db4cd32fc0daa,
title = "Donor-acceptor conjugated polymers based on p- and o-benzodifuranone and thiophene derivatives: electrochemical preparation and optical and electronic properties",
abstract = "A series of pi-conjugated polymers consisting of bis-EDOT or bis-EDTT units and p- or o-diphenylbenzodifuranones have been prepared electrochemically. The monomers and polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. The monomers were synthesized from 3,4-ethylenedioxythien-2-yl or 3,4-ethylenedithiathien-2-yl trimethylstannane and 3,7-bis(4-bromophenyl)benzo[1,2-b:4,5-b']difuran-2,6-dione or 3,6-bis(4-bromophenyl)benzo[1,2-b:6,5-b']difuran-2,7-dione using Stile coupling. The polymers exhibit broad absorption bands, and strong donor-acceptor characteristics with very small band gaps (in a range from 0.40 to 1.20 eV). Electrochemically grown polymer thin films exhibit reversible behavior under oxidative and reductive conditions. Under reduction, the polymer films show color changes from dark to almost transparent.",
keywords = "monomers , conjugated polymers , o-benzodifuranone , thiophene derivatives",
author = "Kai Zhang and Bernd Tieke and Forgie, {John C.} and Filipe Vilela and Skabara, {Peter J.}",
year = "2012",
month = "1",
day = "24",
doi = "10.1021/ma202387t",
language = "English",
volume = "45",
pages = "743--750",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "2",

}

Donor-acceptor conjugated polymers based on p- and o-benzodifuranone and thiophene derivatives : electrochemical preparation and optical and electronic properties. / Zhang, Kai; Tieke, Bernd; Forgie, John C.; Vilela, Filipe; Skabara, Peter J.

In: Macromolecules, Vol. 45, No. 2, 24.01.2012, p. 743-750.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Donor-acceptor conjugated polymers based on p- and o-benzodifuranone and thiophene derivatives

T2 - Macromolecules

AU - Zhang, Kai

AU - Tieke, Bernd

AU - Forgie, John C.

AU - Vilela, Filipe

AU - Skabara, Peter J.

PY - 2012/1/24

Y1 - 2012/1/24

N2 - A series of pi-conjugated polymers consisting of bis-EDOT or bis-EDTT units and p- or o-diphenylbenzodifuranones have been prepared electrochemically. The monomers and polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. The monomers were synthesized from 3,4-ethylenedioxythien-2-yl or 3,4-ethylenedithiathien-2-yl trimethylstannane and 3,7-bis(4-bromophenyl)benzo[1,2-b:4,5-b']difuran-2,6-dione or 3,6-bis(4-bromophenyl)benzo[1,2-b:6,5-b']difuran-2,7-dione using Stile coupling. The polymers exhibit broad absorption bands, and strong donor-acceptor characteristics with very small band gaps (in a range from 0.40 to 1.20 eV). Electrochemically grown polymer thin films exhibit reversible behavior under oxidative and reductive conditions. Under reduction, the polymer films show color changes from dark to almost transparent.

AB - A series of pi-conjugated polymers consisting of bis-EDOT or bis-EDTT units and p- or o-diphenylbenzodifuranones have been prepared electrochemically. The monomers and polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. The monomers were synthesized from 3,4-ethylenedioxythien-2-yl or 3,4-ethylenedithiathien-2-yl trimethylstannane and 3,7-bis(4-bromophenyl)benzo[1,2-b:4,5-b']difuran-2,6-dione or 3,6-bis(4-bromophenyl)benzo[1,2-b:6,5-b']difuran-2,7-dione using Stile coupling. The polymers exhibit broad absorption bands, and strong donor-acceptor characteristics with very small band gaps (in a range from 0.40 to 1.20 eV). Electrochemically grown polymer thin films exhibit reversible behavior under oxidative and reductive conditions. Under reduction, the polymer films show color changes from dark to almost transparent.

KW - monomers

KW - conjugated polymers

KW - o-benzodifuranone

KW - thiophene derivatives

UR - http://www.scopus.com/inward/record.url?scp=84856137611&partnerID=8YFLogxK

U2 - 10.1021/ma202387t

DO - 10.1021/ma202387t

M3 - Article

VL - 45

SP - 743

EP - 750

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 2

ER -