Synthesis of acenaphthyl and phenanthrene based fused-aromatic thienopyrazine co-polymers for photovoltaic and thin film transistor applications

Rajib Mondal; Nobuyuki Miyaki; Hector A. Becerril; Joseph E. Norton; Jack Parmer; Alex C. Mayer; Ming L. Tang; Jean Luc Brédas; Michael D. McGehee; Zhenan Bao

doi:10.1021/cm900788e

Synthesis of acenaphthyl and phenanthrene based fused-aromatic thienopyrazine co-polymers for photovoltaic and thin film transistor applications

Rajib Mondal, Nobuyuki Miyaki, Hector A. Becerril, Joseph E. Norton, Jack Parmer, Alex C. Mayer, Ming L. Tang, Jean Luc Brédas, Michael D. McGehee, Zhenan Bao^*

^*Corresponding author for this work

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

112 Scopus citations

Abstract

Dithiophene and fluorene co-polymers containing fused aromatic thieno[3,4-b]pyrazine moieties were synthesized for organic thin film transistor (OTFT) and organic photovoltaic (OPV) applications. Suzuki and Stille polycondensation reactions were used for the polymerization. The band gap (E_g) of the polymers was tuned in the range of 1.15-1.6 eV to match the solar spectrum. Density functional theory calculations were carried out to rationalize the low band gaps. These polymers showed field effect mobility (μ) as high as 0.2 cm²/(V.s) with an on/off ratio as high as 10⁶ in OTFT devices. Interestingly, one polymer in this class also showed ambipolar charge transport. Power conversion efficiency (PCE) up to 1.3% was achieved in bulk heterojunction solar cells, indicating that these materials are promising for OPV applications.

Original language	English (US)
Pages (from-to)	3618-3628
Number of pages	11
Journal	Chemistry of Materials
Volume	21
Issue number	15
DOIs	https://doi.org/10.1021/cm900788e
State	Published - Aug 11 2009
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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title = "Synthesis of acenaphthyl and phenanthrene based fused-aromatic thienopyrazine co-polymers for photovoltaic and thin film transistor applications",

abstract = "Dithiophene and fluorene co-polymers containing fused aromatic thieno[3,4-b]pyrazine moieties were synthesized for organic thin film transistor (OTFT) and organic photovoltaic (OPV) applications. Suzuki and Stille polycondensation reactions were used for the polymerization. The band gap (Eg) of the polymers was tuned in the range of 1.15-1.6 eV to match the solar spectrum. Density functional theory calculations were carried out to rationalize the low band gaps. These polymers showed field effect mobility (μ) as high as 0.2 cm2/(V.s) with an on/off ratio as high as 106 in OTFT devices. Interestingly, one polymer in this class also showed ambipolar charge transport. Power conversion efficiency (PCE) up to 1.3% was achieved in bulk heterojunction solar cells, indicating that these materials are promising for OPV applications.",

author = "Rajib Mondal and Nobuyuki Miyaki and Becerril, {Hector A.} and Norton, {Joseph E.} and Jack Parmer and Mayer, {Alex C.} and Tang, {Ming L.} 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 Stanford Center for Polymer Interfaces and Macromolecular Assemblies (CPIMA). N.M. acknowledges support from JSR Corp., Japan. The work at Georgia Tech was also partly supported by the Office of Naval Research. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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language = "English (US)",

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T1 - Synthesis of acenaphthyl and phenanthrene based fused-aromatic thienopyrazine co-polymers for photovoltaic and thin film transistor applications

AU - Mondal, Rajib

AU - Miyaki, Nobuyuki

AU - Becerril, Hector A.

AU - Norton, Joseph E.

AU - Parmer, Jack

AU - Mayer, Alex C.

AU - Tang, Ming L.

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 Stanford Center for Polymer Interfaces and Macromolecular Assemblies (CPIMA). N.M. acknowledges support from JSR Corp., Japan. The work at Georgia Tech was also partly supported by the Office of Naval Research. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2009/8/11

Y1 - 2009/8/11

N2 - Dithiophene and fluorene co-polymers containing fused aromatic thieno[3,4-b]pyrazine moieties were synthesized for organic thin film transistor (OTFT) and organic photovoltaic (OPV) applications. Suzuki and Stille polycondensation reactions were used for the polymerization. The band gap (Eg) of the polymers was tuned in the range of 1.15-1.6 eV to match the solar spectrum. Density functional theory calculations were carried out to rationalize the low band gaps. These polymers showed field effect mobility (μ) as high as 0.2 cm2/(V.s) with an on/off ratio as high as 106 in OTFT devices. Interestingly, one polymer in this class also showed ambipolar charge transport. Power conversion efficiency (PCE) up to 1.3% was achieved in bulk heterojunction solar cells, indicating that these materials are promising for OPV applications.

AB - Dithiophene and fluorene co-polymers containing fused aromatic thieno[3,4-b]pyrazine moieties were synthesized for organic thin film transistor (OTFT) and organic photovoltaic (OPV) applications. Suzuki and Stille polycondensation reactions were used for the polymerization. The band gap (Eg) of the polymers was tuned in the range of 1.15-1.6 eV to match the solar spectrum. Density functional theory calculations were carried out to rationalize the low band gaps. These polymers showed field effect mobility (μ) as high as 0.2 cm2/(V.s) with an on/off ratio as high as 106 in OTFT devices. Interestingly, one polymer in this class also showed ambipolar charge transport. Power conversion efficiency (PCE) up to 1.3% was achieved in bulk heterojunction solar cells, indicating that these materials are promising for OPV applications.

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Synthesis of acenaphthyl and phenanthrene based fused-aromatic thienopyrazine co-polymers for photovoltaic and thin film transistor applications

Abstract

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