Synthesis and properties of new small band gap conjugated polymers

Methine bridged poly(3,4-ethylenedioxypyrrole)

Jung Hsun Tsai, Wei Ren Tu, Cheng Liang Liu, Wen-Chung Wu, Wen Chang Chen

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Synthesis and electronic properties of new small band gap conjugated polymers, methine-bridged poly(3,4-ethylenedioxy pyrrole) (PEDOP) are reported. Density functional theory (B3LYP with 6-31G basis) are used to obtain the optimizei ground-state geometries and electronic structures of PEDOP and poly [(3,4-ethylenedioxypyrrole-2,5-diyl) methine (PEDOP-M). Theoretical bond length alternation of PEDOP is reduced by incorporating the methine bridge and leads to th band gap reduction from 2.44 to 0.68 eV. The small band gap characteristic of PEDOP-M is further verified by preparing twi conjugated polymers, poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-benzylidene-(2,5-n-benzyl-3, 4-ethylenedioxypyr role-quinodimethanediyl)] (PbEDOP-b) and poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-(p-nitrobenzylidene)-(2, 5-n-benzyl-3,4-ethylenedioxypyrrole-quinodimethanediyl)] (PbEDOP-nb). The optical band gap of PbEDOP-b and PbEDOP nb are 1.77 and 1.45 eV, respectively, while the electrochemical band gap of the former is 1.59 eV. Although the bulky side groups of these two polymers result in a larger band gap than that of PEDOT-M, it indicates the small band gaps of such polymers. The nitrobenzene group could extend the π-conjugation and lead to the smaller band gap of PbEDOP-nb than that of PbEDOP-b. The present study suggests that methine-bridged poly(3,4-ethylenedioxypyrrole) is a class of small band gap polymers.

Original languageEnglish
Pages (from-to)363-369
Number of pages7
JournalPolymer Journal
Volume41
Issue number5
DOIs
Publication statusPublished - 2009 Aug 10

Fingerprint

Conjugated polymers
Energy gap
Pyrroles
Polymers
Nitrobenzene
Optical band gaps
Bond length
Electronic properties
Ground state
Electronic structure
Density functional theory
Geometry

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Materials Chemistry

Cite this

Tsai, Jung Hsun ; Tu, Wei Ren ; Liu, Cheng Liang ; Wu, Wen-Chung ; Chen, Wen Chang. / Synthesis and properties of new small band gap conjugated polymers : Methine bridged poly(3,4-ethylenedioxypyrrole). In: Polymer Journal. 2009 ; Vol. 41, No. 5. pp. 363-369.
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abstract = "Synthesis and electronic properties of new small band gap conjugated polymers, methine-bridged poly(3,4-ethylenedioxy pyrrole) (PEDOP) are reported. Density functional theory (B3LYP with 6-31G basis) are used to obtain the optimizei ground-state geometries and electronic structures of PEDOP and poly [(3,4-ethylenedioxypyrrole-2,5-diyl) methine (PEDOP-M). Theoretical bond length alternation of PEDOP is reduced by incorporating the methine bridge and leads to th band gap reduction from 2.44 to 0.68 eV. The small band gap characteristic of PEDOP-M is further verified by preparing twi conjugated polymers, poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-benzylidene-(2,5-n-benzyl-3, 4-ethylenedioxypyr role-quinodimethanediyl)] (PbEDOP-b) and poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-(p-nitrobenzylidene)-(2, 5-n-benzyl-3,4-ethylenedioxypyrrole-quinodimethanediyl)] (PbEDOP-nb). The optical band gap of PbEDOP-b and PbEDOP nb are 1.77 and 1.45 eV, respectively, while the electrochemical band gap of the former is 1.59 eV. Although the bulky side groups of these two polymers result in a larger band gap than that of PEDOT-M, it indicates the small band gaps of such polymers. The nitrobenzene group could extend the π-conjugation and lead to the smaller band gap of PbEDOP-nb than that of PbEDOP-b. The present study suggests that methine-bridged poly(3,4-ethylenedioxypyrrole) is a class of small band gap polymers.",
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Synthesis and properties of new small band gap conjugated polymers : Methine bridged poly(3,4-ethylenedioxypyrrole). / Tsai, Jung Hsun; Tu, Wei Ren; Liu, Cheng Liang; Wu, Wen-Chung; Chen, Wen Chang.

In: Polymer Journal, Vol. 41, No. 5, 10.08.2009, p. 363-369.

Research output: Contribution to journalArticle

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T1 - Synthesis and properties of new small band gap conjugated polymers

T2 - Methine bridged poly(3,4-ethylenedioxypyrrole)

AU - Tsai, Jung Hsun

AU - Tu, Wei Ren

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AU - Wu, Wen-Chung

AU - Chen, Wen Chang

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N2 - Synthesis and electronic properties of new small band gap conjugated polymers, methine-bridged poly(3,4-ethylenedioxy pyrrole) (PEDOP) are reported. Density functional theory (B3LYP with 6-31G basis) are used to obtain the optimizei ground-state geometries and electronic structures of PEDOP and poly [(3,4-ethylenedioxypyrrole-2,5-diyl) methine (PEDOP-M). Theoretical bond length alternation of PEDOP is reduced by incorporating the methine bridge and leads to th band gap reduction from 2.44 to 0.68 eV. The small band gap characteristic of PEDOP-M is further verified by preparing twi conjugated polymers, poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-benzylidene-(2,5-n-benzyl-3, 4-ethylenedioxypyr role-quinodimethanediyl)] (PbEDOP-b) and poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-(p-nitrobenzylidene)-(2, 5-n-benzyl-3,4-ethylenedioxypyrrole-quinodimethanediyl)] (PbEDOP-nb). The optical band gap of PbEDOP-b and PbEDOP nb are 1.77 and 1.45 eV, respectively, while the electrochemical band gap of the former is 1.59 eV. Although the bulky side groups of these two polymers result in a larger band gap than that of PEDOT-M, it indicates the small band gaps of such polymers. The nitrobenzene group could extend the π-conjugation and lead to the smaller band gap of PbEDOP-nb than that of PbEDOP-b. The present study suggests that methine-bridged poly(3,4-ethylenedioxypyrrole) is a class of small band gap polymers.

AB - Synthesis and electronic properties of new small band gap conjugated polymers, methine-bridged poly(3,4-ethylenedioxy pyrrole) (PEDOP) are reported. Density functional theory (B3LYP with 6-31G basis) are used to obtain the optimizei ground-state geometries and electronic structures of PEDOP and poly [(3,4-ethylenedioxypyrrole-2,5-diyl) methine (PEDOP-M). Theoretical bond length alternation of PEDOP is reduced by incorporating the methine bridge and leads to th band gap reduction from 2.44 to 0.68 eV. The small band gap characteristic of PEDOP-M is further verified by preparing twi conjugated polymers, poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-benzylidene-(2,5-n-benzyl-3, 4-ethylenedioxypyr role-quinodimethanediyl)] (PbEDOP-b) and poly [(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-(p-nitrobenzylidene)-(2, 5-n-benzyl-3,4-ethylenedioxypyrrole-quinodimethanediyl)] (PbEDOP-nb). The optical band gap of PbEDOP-b and PbEDOP nb are 1.77 and 1.45 eV, respectively, while the electrochemical band gap of the former is 1.59 eV. Although the bulky side groups of these two polymers result in a larger band gap than that of PEDOT-M, it indicates the small band gaps of such polymers. The nitrobenzene group could extend the π-conjugation and lead to the smaller band gap of PbEDOP-nb than that of PbEDOP-b. The present study suggests that methine-bridged poly(3,4-ethylenedioxypyrrole) is a class of small band gap polymers.

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