On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%

Jingnan Wu; Zhaoheng Ling; Leandro R. Franco; Sang Young Jeong; Zewdneh Genene; Josué Mena Gómez; Si Chen; Cailing Chen; C. Moyses Araujo; Cleber F. N. Marchiori; Joost Kimpel; Xiaoming Chang; Furkan Halis Isikgor; Qiaonan Chen; Hendrik Faber; Yu Han; Frédéric Laquai; Maojie Zhang; Han Young Woo; Donghong Yu; Thomas D. Anthopoulos; Ergang Wang

doi:10.1002/anie.202302888

On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%

Jingnan Wu, Zhaoheng Ling, Leandro R. Franco, Sang Young Jeong, Zewdneh Genene, Josué Mena Gómez, Si Chen, Cailing Chen, C. Moyses Araujo, Cleber F. N. Marchiori, Joost Kimpel, Xiaoming Chang, Furkan Halis Isikgor, Qiaonan Chen, Hendrik Faber, Yu Han, Frédéric Laquai, Maojie Zhang, Han Young Woo, Donghong YuThomas D. Anthopoulos, Ergang Wang

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

40 Scopus citations

Abstract

The determination of molecular conformation of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of resulting polymer solar cells (PSCs) but have not been well studied yet. Herein, we synthesized two dimeric acceptor materials, DIBP3F-Se and DIBP3F-S, which bridged two segments of Y6-derivatives by selenophene and thiophene, respectively. Theoretical simulation and experimental 1D and 2D NMR spectroscopic studies prove that both dimers exhibit O-shape conformation other than S- or U-shape counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive "conformational lock" mechanism, arising from the intensified intramolecular π-π interaction between the two terminal groups of the dimers. PSCs based on DIBP3F-Se deliver a maximum efficiency of 18.09%, outperforming DIBP3F-S-based cells (16.11%) and ranking among the highest efficiencies for OA-based PSCs. This work demonstrates a facile method to obtain OA conformations and highlights the potential of dimeric acceptors for high-performance PSCs.

Original language	English (US)
Journal	Angewandte Chemie International Edition
DOIs	https://doi.org/10.1002/anie.202302888
State	Published - Jun 28 2023

Bibliographical note

KAUST Repository Item: Exported on 2023-07-07
Acknowledged KAUST grant number(s): OSR-2018-CARF/CCF-3079, OSR-2019-CRG8-4095.3
Acknowledgements: We thank the Swedish Research Council (2016-06146, 2019-04683, 2020-05233), Swedish Research Council Formas, Knut and Alice Wallenberg Foundation (2017.0186, 2016.0059), Swedish Energy Agency (Grant number: P2021-90067) and STandUP for Energy collaboration. Computations/simulations were performed at Chalmers e-Commons (C3SE) and Swedish National Infrastructure for Computing (SNIC) at the National Supercomputer Centre (NSC) at Linköping University. J. W. acknowledges the support from the Chinese Scholarship Council. T.D.A., Z.H., C. C., X.C., F.H.I.,F.L., acknowledge support by the KAUST Office of Sponsored Research (OSR) under Awards No: OSR-2018-CARF/CCF-3079 and No: OSR-2019-CRG8-4095.3. H.Y.W. acknowledges the support from the National Research Foundation of Korea (2019R1A6A1A11044070). Support from Sino-Danish Center (SDC) for Education and Research is fully acknowledged. The 2D NMR measurements were performed at the Swedish NMR Center, in Gothenburg, Sweden. Grateful for the discussion with Prof. Reinhard Wimmer from Aalborg University on a conformational determination.

ASJC Scopus subject areas

General Chemistry
Catalysis

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.202302888

https://repository.kaust.edu.sa/bitstream/10754/692824/1/Angew%20Chem%20Int%20Ed%20-%202023%20-%20Wu%20-%20On%20the%20Conformation%20of%20Dimeric%20Acceptors%20and%20Their%20Polymer%20Solar%20Cells%20with%20Efficiency%20over_removed.pdf

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Wu, J., Ling, Z., Franco, L. R., Jeong, S. Y., Genene, Z., Gómez, J. M., Chen, S., Chen, C., Araujo, C. M., Marchiori, C. F. N., Kimpel, J., Chang, X., Isikgor, F. H., Chen, Q., Faber, H., Han, Y., Laquai, F., Zhang, M., Woo, H. Y., ... Wang, E. (2023). On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202302888

@article{c08031ada63e49e282d8305f4da17f5c,

title = "On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%",

abstract = "The determination of molecular conformation of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of resulting polymer solar cells (PSCs) but have not been well studied yet. Herein, we synthesized two dimeric acceptor materials, DIBP3F-Se and DIBP3F-S, which bridged two segments of Y6-derivatives by selenophene and thiophene, respectively. Theoretical simulation and experimental 1D and 2D NMR spectroscopic studies prove that both dimers exhibit O-shape conformation other than S- or U-shape counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive {"}conformational lock{"} mechanism, arising from the intensified intramolecular π-π interaction between the two terminal groups of the dimers. PSCs based on DIBP3F-Se deliver a maximum efficiency of 18.09%, outperforming DIBP3F-S-based cells (16.11%) and ranking among the highest efficiencies for OA-based PSCs. This work demonstrates a facile method to obtain OA conformations and highlights the potential of dimeric acceptors for high-performance PSCs.",

author = "Jingnan Wu and Zhaoheng Ling and Franco, {Leandro R.} and Jeong, {Sang Young} and Zewdneh Genene and G{\'o}mez, {Josu{\'e} Mena} and Si Chen and Cailing Chen and Araujo, {C. Moyses} and Marchiori, {Cleber F. N.} and Joost Kimpel and Xiaoming Chang and Isikgor, {Furkan Halis} and Qiaonan Chen and Hendrik Faber and Yu Han and Fr{\'e}d{\'e}ric Laquai and Maojie Zhang and Woo, {Han Young} and Donghong Yu and Anthopoulos, {Thomas D.} and Ergang Wang",

note = "KAUST Repository Item: Exported on 2023-07-07 Acknowledged KAUST grant number(s): OSR-2018-CARF/CCF-3079, OSR-2019-CRG8-4095.3 Acknowledgements: We thank the Swedish Research Council (2016-06146, 2019-04683, 2020-05233), Swedish Research Council Formas, Knut and Alice Wallenberg Foundation (2017.0186, 2016.0059), Swedish Energy Agency (Grant number: P2021-90067) and STandUP for Energy collaboration. Computations/simulations were performed at Chalmers e-Commons (C3SE) and Swedish National Infrastructure for Computing (SNIC) at the National Supercomputer Centre (NSC) at Link{\"o}ping University. J. W. acknowledges the support from the Chinese Scholarship Council. T.D.A., Z.H., C. C., X.C., F.H.I.,F.L., acknowledge support by the KAUST Office of Sponsored Research (OSR) under Awards No: OSR-2018-CARF/CCF-3079 and No: OSR-2019-CRG8-4095.3. H.Y.W. acknowledges the support from the National Research Foundation of Korea (2019R1A6A1A11044070). Support from Sino-Danish Center (SDC) for Education and Research is fully acknowledged. The 2D NMR measurements were performed at the Swedish NMR Center, in Gothenburg, Sweden. Grateful for the discussion with Prof. Reinhard Wimmer from Aalborg University on a conformational determination.",

year = "2023",

month = jun,

day = "28",

doi = "10.1002/anie.202302888",

language = "English (US)",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

}

Wu, J, Ling, Z, Franco, LR, Jeong, SY, Genene, Z, Gómez, JM, Chen, S, Chen, C, Araujo, CM, Marchiori, CFN, Kimpel, J, Chang, X , Isikgor, FH, Chen, Q, Faber, H, Han, Y, Laquai, F, Zhang, M, Woo, HY, Yu, D, Anthopoulos, TD & Wang, E 2023, 'On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%', Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202302888

TY - JOUR

T1 - On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%

AU - Wu, Jingnan

AU - Ling, Zhaoheng

AU - Franco, Leandro R.

AU - Jeong, Sang Young

AU - Genene, Zewdneh

AU - Gómez, Josué Mena

AU - Chen, Si

AU - Chen, Cailing

AU - Araujo, C. Moyses

AU - Marchiori, Cleber F. N.

AU - Kimpel, Joost

AU - Chang, Xiaoming

AU - Isikgor, Furkan Halis

AU - Chen, Qiaonan

AU - Faber, Hendrik

AU - Han, Yu

AU - Laquai, Frédéric

AU - Zhang, Maojie

AU - Woo, Han Young

AU - Yu, Donghong

AU - Anthopoulos, Thomas D.

AU - Wang, Ergang

N1 - KAUST Repository Item: Exported on 2023-07-07 Acknowledged KAUST grant number(s): OSR-2018-CARF/CCF-3079, OSR-2019-CRG8-4095.3 Acknowledgements: We thank the Swedish Research Council (2016-06146, 2019-04683, 2020-05233), Swedish Research Council Formas, Knut and Alice Wallenberg Foundation (2017.0186, 2016.0059), Swedish Energy Agency (Grant number: P2021-90067) and STandUP for Energy collaboration. Computations/simulations were performed at Chalmers e-Commons (C3SE) and Swedish National Infrastructure for Computing (SNIC) at the National Supercomputer Centre (NSC) at Linköping University. J. W. acknowledges the support from the Chinese Scholarship Council. T.D.A., Z.H., C. C., X.C., F.H.I.,F.L., acknowledge support by the KAUST Office of Sponsored Research (OSR) under Awards No: OSR-2018-CARF/CCF-3079 and No: OSR-2019-CRG8-4095.3. H.Y.W. acknowledges the support from the National Research Foundation of Korea (2019R1A6A1A11044070). Support from Sino-Danish Center (SDC) for Education and Research is fully acknowledged. The 2D NMR measurements were performed at the Swedish NMR Center, in Gothenburg, Sweden. Grateful for the discussion with Prof. Reinhard Wimmer from Aalborg University on a conformational determination.

PY - 2023/6/28

Y1 - 2023/6/28

N2 - The determination of molecular conformation of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of resulting polymer solar cells (PSCs) but have not been well studied yet. Herein, we synthesized two dimeric acceptor materials, DIBP3F-Se and DIBP3F-S, which bridged two segments of Y6-derivatives by selenophene and thiophene, respectively. Theoretical simulation and experimental 1D and 2D NMR spectroscopic studies prove that both dimers exhibit O-shape conformation other than S- or U-shape counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive "conformational lock" mechanism, arising from the intensified intramolecular π-π interaction between the two terminal groups of the dimers. PSCs based on DIBP3F-Se deliver a maximum efficiency of 18.09%, outperforming DIBP3F-S-based cells (16.11%) and ranking among the highest efficiencies for OA-based PSCs. This work demonstrates a facile method to obtain OA conformations and highlights the potential of dimeric acceptors for high-performance PSCs.

AB - The determination of molecular conformation of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of resulting polymer solar cells (PSCs) but have not been well studied yet. Herein, we synthesized two dimeric acceptor materials, DIBP3F-Se and DIBP3F-S, which bridged two segments of Y6-derivatives by selenophene and thiophene, respectively. Theoretical simulation and experimental 1D and 2D NMR spectroscopic studies prove that both dimers exhibit O-shape conformation other than S- or U-shape counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive "conformational lock" mechanism, arising from the intensified intramolecular π-π interaction between the two terminal groups of the dimers. PSCs based on DIBP3F-Se deliver a maximum efficiency of 18.09%, outperforming DIBP3F-S-based cells (16.11%) and ranking among the highest efficiencies for OA-based PSCs. This work demonstrates a facile method to obtain OA conformations and highlights the potential of dimeric acceptors for high-performance PSCs.

UR - http://hdl.handle.net/10754/692824

UR - https://onlinelibrary.wiley.com/doi/10.1002/anie.202302888

U2 - 10.1002/anie.202302888

DO - 10.1002/anie.202302888

M3 - Article

C2 - 37380618

SN - 1433-7851

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

On the Conformation of Dimeric Acceptors and Their Polymer Solar Cells with Efficiency over 18%

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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