Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v

Julien Warnan; Clement Cabanetos; Romain Bude; Abdulrahman El Labban; Liang Li; Pierre Beaujuge

doi:10.1021/cm5002303

Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v

Julien Warnan, Clement Cabanetos, Romain Bude, Abdulrahman El Labban, Liang Li, Pierre Beaujuge

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

75 Scopus citations

Abstract

Poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymer donors yield some of the highest open-circuit voltages (V OC, ca. 0.9 V) and fill factors (FF, ca. 70%) in conventional bulk-heterojunction (BHJ) solar cells with PCBM acceptors. Recent work has shown that the incorporation of ring substituents into the side chains of the BDT motifs in PBDTTPD can induce subtle variations in material properties, resulting in an increase of the BHJ device VOC to ∼1 V. In this contribution, we report on the synthesis of N-alkyloyl-substituted TPD motifs (TPD(CO)) and show that the electron-deficient motifs can further lower both the polymer LUMO and HOMO levels, yielding device VOC > 1 V (up to ca. 1.1 V) in BHJ solar cells with PCBM. Despite the high VOC achieved (i.e., low polymer HOMO), BHJ devices cast from TPD(CO)-based polymer donors can reach power conversion efficiencies (PCEs) of up to 6.7%, making these promising systems for use in the high-band-gap cell of tandem solar cells. © 2014 American Chemical Society.

Original language	English (US)
Pages (from-to)	2829-2835
Number of pages	7
Journal	Chemistry of Materials
Volume	26
Issue number	9
DOIs	https://doi.org/10.1021/cm5002303
State	Published - Apr 21 2014

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). The authors thank KAUST Analytical Core Laboratories for mass spectrometry, SEC measurements, and elemental analyses, and Sandra Seywald (MPIP - Mainz, Germany) for additional SEC measurements. The authors thank the Advanced Imaging and Characterization Laboratories at KAUST for technical support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.

ASJC Scopus subject areas

Materials Chemistry
General Chemical Engineering
General Chemistry

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10.1021/cm5002303

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@article{3835ae0c16ef48d195c26f7ad6ef40fa,

title = "Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v",

abstract = "Poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymer donors yield some of the highest open-circuit voltages (V OC, ca. 0.9 V) and fill factors (FF, ca. 70%) in conventional bulk-heterojunction (BHJ) solar cells with PCBM acceptors. Recent work has shown that the incorporation of ring substituents into the side chains of the BDT motifs in PBDTTPD can induce subtle variations in material properties, resulting in an increase of the BHJ device VOC to ∼1 V. In this contribution, we report on the synthesis of N-alkyloyl-substituted TPD motifs (TPD(CO)) and show that the electron-deficient motifs can further lower both the polymer LUMO and HOMO levels, yielding device VOC > 1 V (up to ca. 1.1 V) in BHJ solar cells with PCBM. Despite the high VOC achieved (i.e., low polymer HOMO), BHJ devices cast from TPD(CO)-based polymer donors can reach power conversion efficiencies (PCEs) of up to 6.7%, making these promising systems for use in the high-band-gap cell of tandem solar cells. {\textcopyright} 2014 American Chemical Society.",

author = "Julien Warnan and Clement Cabanetos and Romain Bude and {El Labban}, Abdulrahman and Liang Li and Pierre Beaujuge",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). The authors thank KAUST Analytical Core Laboratories for mass spectrometry, SEC measurements, and elemental analyses, and Sandra Seywald (MPIP - Mainz, Germany) for additional SEC measurements. The authors thank the Advanced Imaging and Characterization Laboratories at KAUST for technical support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.",

year = "2014",

month = apr,

day = "21",

doi = "10.1021/cm5002303",

language = "English (US)",

volume = "26",

pages = "2829--2835",

journal = "Chemistry of Materials",

issn = "0897-4756",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v

AU - Warnan, Julien

AU - Cabanetos, Clement

AU - Bude, Romain

AU - El Labban, Abdulrahman

AU - Li, Liang

AU - Beaujuge, Pierre

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The authors acknowledge financial support under Baseline Research Funding from King Abdullah University of Science and Technology (KAUST). The authors thank KAUST Analytical Core Laboratories for mass spectrometry, SEC measurements, and elemental analyses, and Sandra Seywald (MPIP - Mainz, Germany) for additional SEC measurements. The authors thank the Advanced Imaging and Characterization Laboratories at KAUST for technical support. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated by Stanford University on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences.

PY - 2014/4/21

Y1 - 2014/4/21

N2 - Poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymer donors yield some of the highest open-circuit voltages (V OC, ca. 0.9 V) and fill factors (FF, ca. 70%) in conventional bulk-heterojunction (BHJ) solar cells with PCBM acceptors. Recent work has shown that the incorporation of ring substituents into the side chains of the BDT motifs in PBDTTPD can induce subtle variations in material properties, resulting in an increase of the BHJ device VOC to ∼1 V. In this contribution, we report on the synthesis of N-alkyloyl-substituted TPD motifs (TPD(CO)) and show that the electron-deficient motifs can further lower both the polymer LUMO and HOMO levels, yielding device VOC > 1 V (up to ca. 1.1 V) in BHJ solar cells with PCBM. Despite the high VOC achieved (i.e., low polymer HOMO), BHJ devices cast from TPD(CO)-based polymer donors can reach power conversion efficiencies (PCEs) of up to 6.7%, making these promising systems for use in the high-band-gap cell of tandem solar cells. © 2014 American Chemical Society.

AB - Poly(benzo[1,2-b:4,5-b′]dithiophene-thieno[3,4-c]pyrrole-4,6-dione) (PBDTTPD) polymer donors yield some of the highest open-circuit voltages (V OC, ca. 0.9 V) and fill factors (FF, ca. 70%) in conventional bulk-heterojunction (BHJ) solar cells with PCBM acceptors. Recent work has shown that the incorporation of ring substituents into the side chains of the BDT motifs in PBDTTPD can induce subtle variations in material properties, resulting in an increase of the BHJ device VOC to ∼1 V. In this contribution, we report on the synthesis of N-alkyloyl-substituted TPD motifs (TPD(CO)) and show that the electron-deficient motifs can further lower both the polymer LUMO and HOMO levels, yielding device VOC > 1 V (up to ca. 1.1 V) in BHJ solar cells with PCBM. Despite the high VOC achieved (i.e., low polymer HOMO), BHJ devices cast from TPD(CO)-based polymer donors can reach power conversion efficiencies (PCEs) of up to 6.7%, making these promising systems for use in the high-band-gap cell of tandem solar cells. © 2014 American Chemical Society.

UR - http://hdl.handle.net/10754/563544

UR - https://pubs.acs.org/doi/10.1021/cm5002303

UR - http://www.scopus.com/inward/record.url?scp=84900417726&partnerID=8YFLogxK

U2 - 10.1021/cm5002303

DO - 10.1021/cm5002303

M3 - Article

SN - 0897-4756

VL - 26

SP - 2829

EP - 2835

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 9

ER -

Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v

Abstract

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CCDC 1029500: Experimental Crystal Structure Determination : 1,3-Dibromo-5-butyryl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

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Electron-deficient N-alkyloyl derivatives of thieno[3,4-c]pyrrole-4,6-dione yield efficient polymer solar cells with open-circuit voltages > 1 v

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1029500: Experimental Crystal Structure Determination : 1,3-Dibromo-5-butyryl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Cite this