Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP): synthesis, optical and electronic properties

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

Research output: Contribution to journal › Article

25 Citations (Scopus)

Abstract

A series of 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) derivatives carrying thienyl-, 3,4-ethylenedioxy-thienyl- (EDOT-) and 3,4-ethylenedithiathienyl- (EDTT-) substituent groups have been synthesized and electrochemically polymerized. The polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. It was found that the growth of the polymers proceeded as random coupling of the thiophene groups in the 2-,3-,5-, and 6-positions of the DPP chromophore. In the cross-linked polymers, conjugated sequences were only built through coupling of thiophene groups in 3,6-positions, and separated by non-conjugated sequences through coupling with thiophene units in other positions of the DPP core.
LanguageEnglish
Pages6107-6114
Number of pages8
JournalPolymer
Volume51
Issue number26
DOIs
Publication statusPublished - 10 Dec 2010

Fingerprint

Thiophenes
Pyrroles
Thiophene
Electronic properties
Polymers
Optical properties
Conjugated polymers
Chromophores
Ultraviolet spectroscopy
Absorption spectroscopy
Cyclic voltammetry
Derivatives

Keywords

  • cross-linked polymers
  • tetra-substituted
  • synthesis
  • electronic properties
  • optical
  • pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  • DPP
  • electropolymerization

Cite this

Zhang, Kai ; Tieke, Bernd ; Forgie, John C. ; Vilela, Filipe ; Parkinson, John A. ; Skabara, Peter J. / Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) : synthesis, optical and electronic properties. In: Polymer. 2010 ; Vol. 51, No. 26. pp. 6107-6114.
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title = "Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP): synthesis, optical and electronic properties",
abstract = "A series of 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) derivatives carrying thienyl-, 3,4-ethylenedioxy-thienyl- (EDOT-) and 3,4-ethylenedithiathienyl- (EDTT-) substituent groups have been synthesized and electrochemically polymerized. The polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. It was found that the growth of the polymers proceeded as random coupling of the thiophene groups in the 2-,3-,5-, and 6-positions of the DPP chromophore. In the cross-linked polymers, conjugated sequences were only built through coupling of thiophene groups in 3,6-positions, and separated by non-conjugated sequences through coupling with thiophene units in other positions of the DPP core.",
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author = "Kai Zhang and Bernd Tieke and Forgie, {John C.} and Filipe Vilela and Parkinson, {John A.} and Skabara, {Peter J.}",
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Zhang, K, Tieke, B, Forgie, JC, Vilela, F, Parkinson, JA & Skabara, PJ 2010, 'Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP): synthesis, optical and electronic properties' Polymer, vol. 51, no. 26, pp. 6107-6114. https://doi.org/10.1016/j.polymer.2010.10.054

Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) : synthesis, optical and electronic properties. / Zhang, Kai; Tieke, Bernd; Forgie, John C.; Vilela, Filipe; Parkinson, John A.; Skabara, Peter J.

In: Polymer, Vol. 51, No. 26, 10.12.2010, p. 6107-6114.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP)

T2 - Polymer

AU - Zhang, Kai

AU - Tieke, Bernd

AU - Forgie, John C.

AU - Vilela, Filipe

AU - Parkinson, John A.

AU - Skabara, Peter J.

PY - 2010/12/10

Y1 - 2010/12/10

N2 - A series of 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) derivatives carrying thienyl-, 3,4-ethylenedioxy-thienyl- (EDOT-) and 3,4-ethylenedithiathienyl- (EDTT-) substituent groups have been synthesized and electrochemically polymerized. The polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. It was found that the growth of the polymers proceeded as random coupling of the thiophene groups in the 2-,3-,5-, and 6-positions of the DPP chromophore. In the cross-linked polymers, conjugated sequences were only built through coupling of thiophene groups in 3,6-positions, and separated by non-conjugated sequences through coupling with thiophene units in other positions of the DPP core.

AB - A series of 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP) derivatives carrying thienyl-, 3,4-ethylenedioxy-thienyl- (EDOT-) and 3,4-ethylenedithiathienyl- (EDTT-) substituent groups have been synthesized and electrochemically polymerized. The polymers were investigated using UV/vis absorption spectroscopy and cyclic voltammetry. It was found that the growth of the polymers proceeded as random coupling of the thiophene groups in the 2-,3-,5-, and 6-positions of the DPP chromophore. In the cross-linked polymers, conjugated sequences were only built through coupling of thiophene groups in 3,6-positions, and separated by non-conjugated sequences through coupling with thiophene units in other positions of the DPP core.

KW - cross-linked polymers

KW - tetra-substituted

KW - synthesis

KW - electronic properties

KW - optical

KW - pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

KW - DPP

KW - electropolymerization

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U2 - 10.1016/j.polymer.2010.10.054

DO - 10.1016/j.polymer.2010.10.054

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EP - 6114

JO - Polymer

JF - Polymer

SN - 0032-3861

IS - 26

ER -

Zhang K, Tieke B, Forgie JC, Vilela F, Parkinson JA, Skabara PJ. Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP): synthesis, optical and electronic properties. Polymer. 2010 Dec 10;51(26):6107-6114. https://doi.org/10.1016/j.polymer.2010.10.054

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