Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications

Rajib Mondal; Hector A. Becerril; Eric Verploegen; Dongwook Kim; Joseph E. Norton; Sangwon Ko; Nobuyuki Miyaki; Sangjun Lee; Michael F. Toney; Jean Luc Brédas; Michael D. McGehee; Zhenan Bao

doi:10.1039/c0jm00903b

Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications

Rajib Mondal, Hector A. Becerril, Eric Verploegen, Dongwook Kim, Joseph E. Norton, Sangwon Ko, Nobuyuki Miyaki, Sangjun Lee, Michael F. Toney, Jean Luc Brédas, Michael D. McGehee, Zhenan Bao^*

^*Corresponding author for this work

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

93 Scopus citations

Abstract

Thiophene enriched fused-aromatic thieno[3,4-b]pyrazine systems were designed and employed to produce low band gap polymers (E_g = 1.0-1.4 eV) when copolymerized with fluorene and cyclopentadithiophene. The copolymers are mainly investigated for organic thin film transistor and organic photovoltaic applications. Molecular packing in the thin films of these polymers was investigated using Grazing incidence X-ray Scattering. Although both fluorene and cyclopentadithiophene polymers follow similar face to face π-π stacking, the latter polymers show much smaller lamellar d-spacings due to side-chain interdigitation between the lamellae. This lead to the higher charge carrier mobilities in cyclopentadithiophene polymers (up to 0.044 cm2/V.s) compared to fluorene polymers (up to 8.1 × 10^-3 cm²/V.s). Power conversion efficiency of 1.4% was achieved using fluorene copolymer in solar cells with a fullerene derivative as an acceptor. Although the cyclopentadithiophene polymers show lower band gaps with higher absorption coefficients compared to fluorene copolymers, but the power conversion efficiencies in solar cells of these polymers are low due to their low ionization potentials.

Original language	English (US)
Pages (from-to)	5823-5834
Number of pages	12
Journal	Journal of Materials Chemistry
Volume	20
Issue number	28
DOIs	https://doi.org/10.1039/c0jm00903b
State	Published - Jul 28 2010
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): KUS-C1-015-21
Acknowledgements: This publication was partially based on work supported by the Center for Advanced Molecular Photovoltaics, Award No KUS-C1-015-21, made by King Abdullah University of Science and Technology (KAUST). We also acknowledge support from the Global Climate and Energy Program (GCEP) and the facility usage at the Stanford Center for Polymer Interfaces and Macromolecular Assemblies (CPIMA). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. R.M thanks Jack E. Parmer, George Margulis, and Eric Hoke for their help.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

ASJC Scopus subject areas

General Chemistry
Materials Chemistry

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10.1039/c0jm00903b

Cite this

Mondal, R., Becerril, H. A., Verploegen, E., Kim, D., Norton, J. E., Ko, S., Miyaki, N., Lee, S., Toney, M. F., Brédas, J. L., McGehee, M. D., & Bao, Z. (2010). Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications. Journal of Materials Chemistry, 20(28), 5823-5834. https://doi.org/10.1039/c0jm00903b

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title = "Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications",

abstract = "Thiophene enriched fused-aromatic thieno[3,4-b]pyrazine systems were designed and employed to produce low band gap polymers (Eg = 1.0-1.4 eV) when copolymerized with fluorene and cyclopentadithiophene. The copolymers are mainly investigated for organic thin film transistor and organic photovoltaic applications. Molecular packing in the thin films of these polymers was investigated using Grazing incidence X-ray Scattering. Although both fluorene and cyclopentadithiophene polymers follow similar face to face π-π stacking, the latter polymers show much smaller lamellar d-spacings due to side-chain interdigitation between the lamellae. This lead to the higher charge carrier mobilities in cyclopentadithiophene polymers (up to 0.044 cm2/V.s) compared to fluorene polymers (up to 8.1 × 10-3 cm2/V.s). Power conversion efficiency of 1.4% was achieved using fluorene copolymer in solar cells with a fullerene derivative as an acceptor. Although the cyclopentadithiophene polymers show lower band gaps with higher absorption coefficients compared to fluorene copolymers, but the power conversion efficiencies in solar cells of these polymers are low due to their low ionization potentials.",

author = "Rajib Mondal and Becerril, {Hector A.} and Eric Verploegen and Dongwook Kim and Norton, {Joseph E.} and Sangwon Ko and Nobuyuki Miyaki and Sangjun Lee and Toney, {Michael F.} and Br{\'e}das, {Jean Luc} and McGehee, {Michael D.} and Zhenan Bao",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: This publication was partially based on work supported by the Center for Advanced Molecular Photovoltaics, Award No KUS-C1-015-21, made by King Abdullah University of Science and Technology (KAUST). We also acknowledge support from the Global Climate and Energy Program (GCEP) and the facility usage at the Stanford Center for Polymer Interfaces and Macromolecular Assemblies (CPIMA). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. R.M thanks Jack E. Parmer, George Margulis, and Eric Hoke for their help. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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Mondal, R, Becerril, HA, Verploegen, E, Kim, D, Norton, JE, Ko, S, Miyaki, N, Lee, S, Toney, MF, Brédas, JL, McGehee, MD & Bao, Z 2010, 'Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications', Journal of Materials Chemistry, vol. 20, no. 28, pp. 5823-5834. https://doi.org/10.1039/c0jm00903b

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T1 - Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications

AU - Mondal, Rajib

AU - Becerril, Hector A.

AU - Verploegen, Eric

AU - Kim, Dongwook

AU - Norton, Joseph E.

AU - Ko, Sangwon

AU - Miyaki, Nobuyuki

AU - Lee, Sangjun

AU - Toney, Michael F.

AU - Brédas, Jean Luc

AU - McGehee, Michael D.

AU - Bao, Zhenan

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): KUS-C1-015-21 Acknowledgements: This publication was partially based on work supported by the Center for Advanced Molecular Photovoltaics, Award No KUS-C1-015-21, made by King Abdullah University of Science and Technology (KAUST). We also acknowledge support from the Global Climate and Energy Program (GCEP) and the facility usage at the Stanford Center for Polymer Interfaces and Macromolecular Assemblies (CPIMA). Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource, a national user facility operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. R.M thanks Jack E. Parmer, George Margulis, and Eric Hoke for their help. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2010/7/28

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N2 - Thiophene enriched fused-aromatic thieno[3,4-b]pyrazine systems were designed and employed to produce low band gap polymers (Eg = 1.0-1.4 eV) when copolymerized with fluorene and cyclopentadithiophene. The copolymers are mainly investigated for organic thin film transistor and organic photovoltaic applications. Molecular packing in the thin films of these polymers was investigated using Grazing incidence X-ray Scattering. Although both fluorene and cyclopentadithiophene polymers follow similar face to face π-π stacking, the latter polymers show much smaller lamellar d-spacings due to side-chain interdigitation between the lamellae. This lead to the higher charge carrier mobilities in cyclopentadithiophene polymers (up to 0.044 cm2/V.s) compared to fluorene polymers (up to 8.1 × 10-3 cm2/V.s). Power conversion efficiency of 1.4% was achieved using fluorene copolymer in solar cells with a fullerene derivative as an acceptor. Although the cyclopentadithiophene polymers show lower band gaps with higher absorption coefficients compared to fluorene copolymers, but the power conversion efficiencies in solar cells of these polymers are low due to their low ionization potentials.

AB - Thiophene enriched fused-aromatic thieno[3,4-b]pyrazine systems were designed and employed to produce low band gap polymers (Eg = 1.0-1.4 eV) when copolymerized with fluorene and cyclopentadithiophene. The copolymers are mainly investigated for organic thin film transistor and organic photovoltaic applications. Molecular packing in the thin films of these polymers was investigated using Grazing incidence X-ray Scattering. Although both fluorene and cyclopentadithiophene polymers follow similar face to face π-π stacking, the latter polymers show much smaller lamellar d-spacings due to side-chain interdigitation between the lamellae. This lead to the higher charge carrier mobilities in cyclopentadithiophene polymers (up to 0.044 cm2/V.s) compared to fluorene polymers (up to 8.1 × 10-3 cm2/V.s). Power conversion efficiency of 1.4% was achieved using fluorene copolymer in solar cells with a fullerene derivative as an acceptor. Although the cyclopentadithiophene polymers show lower band gaps with higher absorption coefficients compared to fluorene copolymers, but the power conversion efficiencies in solar cells of these polymers are low due to their low ionization potentials.

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Thiophene-rich fused-aromatic thienopyrazine acceptor for donor-acceptor low band-gap polymers for OTFT and polymer solar cell applications

Abstract

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