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; Si Chen; Cailing Chen; C. Moyses Araujo; Cleber F.N. Marchiori; Joost Kimpel; Xiaoming Chang; Furkan H. 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, Si Chen, Cailing Chen, C. Moyses Araujo, Cleber F.N. Marchiori, Joost Kimpel, Xiaoming Chang, Furkan H. 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

50 Citations (Scopus)

Abstract

The determination of molecular conformations of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of their 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-shaped conformations other than S- or U-shaped counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive “conformational lock” mechanism, arising from the intensified intramolecular π–π interactions among their two terminal groups within 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
Article number	e202302888
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	45
DOIs	https://doi.org/10.1002/anie.202302888
Publication status	Published - 2023 Nov 6

Bibliographical note

Publisher Copyright:
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Keywords

Acceptor
Molecular Conformation
Oligomer
Selenophene
Solar Cells

ASJC Scopus subject areas

Catalysis
General Chemistry

UN SDGs

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

Access to Document

10.1002/anie.202302888

Cite this

Wu, J., Ling, Z., Franco, L. R., Jeong, S. Y., Genene, Z., Mena, J., 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, 62(45), Article e202302888. https://doi.org/10.1002/anie.202302888

Wu, J, Ling, Z, Franco, LR, Jeong, SY, Genene, Z, Mena, J, 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, vol. 62, no. 45, e202302888. https://doi.org/10.1002/anie.202302888

@article{cbc4c5e6a11c4cbc9ef3353d9216241b,

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

abstract = "The determination of molecular conformations of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of their 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-shaped conformations other than S- or U-shaped counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive “conformational lock” mechanism, arising from the intensified intramolecular π–π interactions among their two terminal groups within 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.",

keywords = "Acceptor, Molecular Conformation, Oligomer, Selenophene, Solar Cells",

author = "Jingnan Wu and Zhaoheng Ling and Franco, {Leandro R.} and Jeong, {Sang Young} and Zewdneh Genene and 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 H.} 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 = "Publisher Copyright: {\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

year = "2023",

month = nov,

day = "6",

doi = "10.1002/anie.202302888",

language = "English",

volume = "62",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "45",

}

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 - Mena, Josué

AU - Chen, Si

AU - Chen, Cailing

AU - Araujo, C. Moyses

AU - Marchiori, Cleber F.N.

AU - Kimpel, Joost

AU - Chang, Xiaoming

AU - Isikgor, Furkan H.

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

PY - 2023/11/6

Y1 - 2023/11/6

N2 - The determination of molecular conformations of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of their 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-shaped conformations other than S- or U-shaped counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive “conformational lock” mechanism, arising from the intensified intramolecular π–π interactions among their two terminal groups within 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 conformations of oligomeric acceptors (OAs) and their impact on molecular packing are crucial for understanding the photovoltaic performance of their 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-shaped conformations other than S- or U-shaped counter-ones. Notably, this O-shaped conformation is likely governed by a distinctive “conformational lock” mechanism, arising from the intensified intramolecular π–π interactions among their two terminal groups within 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.

KW - Acceptor

KW - Molecular Conformation

KW - Oligomer

KW - Selenophene

KW - Solar Cells

UR - http://www.scopus.com/inward/record.url?scp=85165198230&partnerID=8YFLogxK

U2 - 10.1002/anie.202302888

DO - 10.1002/anie.202302888

M3 - Article

AN - SCOPUS:85165198230

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 45

M1 - e202302888

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this