Verifying the structure-property-performance relationship of Y6-based small molecule acceptors by alkoxy-side chain isomerization and conjugated skeleton asymmetry
Abstract
Non-fullerene small molecule acceptors (NF-SMAs) such as Y6 derivatives were the current working horse for the top performing polymer solar cells (PSCs). For this reason, numerous chemical modifications have been explored for establishing structure–property-performance relationship for Y6-based NF-SMAs. In this work, we explored the isomerization on asymmetrical Y6 derivatives by varying the position of alkoxy side chain on the thiophene linkage between the core and one of the end groups of Y6. The isomers with differences in conformational restriction raised by noncovalent interactions as well as steric hindrance revealed distinctive behavior in crystallization and polymorphism, which led to a significant contrast in PSC performances. Here the X-TO1 molecule with alkoxy side chain facing the end group (outward) displayed preferred molecular configuration and polymorph, delivering power conversion efficiency (PCE) of 15.63%, while its isomer X-TO2 showed coexisted polymorphs significantly increased the charge recombination in the PSC devices led to a low PCE around 3%. This structure–property-performance relationship not only highlighted the elegancy of isomerization in tuning the photovoltaic performances but also identified polymorphism as one of the causes for impairing photovoltaic performances of PSCs.
- Authors:
-
- Sichuan Univ., Chengdu (China)
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Publication Date:
- Research Org.:
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC); Foundation of State Key Laboratory of Polymer Materials Engineering; Fundamental Research Funds for the Central Universities
- OSTI Identifier:
- 1890207
- Report Number(s):
- BNL-223513-2022-JAAM
Journal ID: ISSN 1385-8947
- Grant/Contract Number:
- SC0012704; 21825502; 22075190; 21905185; 22105135; 2020ZYD004; SKLPME 2017-2-04
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemical Engineering Journal
- Additional Journal Information:
- Journal Volume: 441; Journal ID: ISSN 1385-8947
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; isomerization; asymmetry; Y6 derivative; polymorph; structure-property-performance relationship
Citation Formats
Xiang, Wenxiang, Xu, Xiaopeng, Huang, Yanping, Yu, Liyang, Li, Ruipeng, Jiang, Yu, and Peng, Qiang. Verifying the structure-property-performance relationship of Y6-based small molecule acceptors by alkoxy-side chain isomerization and conjugated skeleton asymmetry. United States: N. p., 2022.
Web. doi:10.1016/j.cej.2022.136058.
Xiang, Wenxiang, Xu, Xiaopeng, Huang, Yanping, Yu, Liyang, Li, Ruipeng, Jiang, Yu, & Peng, Qiang. Verifying the structure-property-performance relationship of Y6-based small molecule acceptors by alkoxy-side chain isomerization and conjugated skeleton asymmetry. United States. https://doi.org/10.1016/j.cej.2022.136058
Xiang, Wenxiang, Xu, Xiaopeng, Huang, Yanping, Yu, Liyang, Li, Ruipeng, Jiang, Yu, and Peng, Qiang. Mon .
"Verifying the structure-property-performance relationship of Y6-based small molecule acceptors by alkoxy-side chain isomerization and conjugated skeleton asymmetry". United States. https://doi.org/10.1016/j.cej.2022.136058. https://www.osti.gov/servlets/purl/1890207.
@article{osti_1890207,
title = {Verifying the structure-property-performance relationship of Y6-based small molecule acceptors by alkoxy-side chain isomerization and conjugated skeleton asymmetry},
author = {Xiang, Wenxiang and Xu, Xiaopeng and Huang, Yanping and Yu, Liyang and Li, Ruipeng and Jiang, Yu and Peng, Qiang},
abstractNote = {Non-fullerene small molecule acceptors (NF-SMAs) such as Y6 derivatives were the current working horse for the top performing polymer solar cells (PSCs). For this reason, numerous chemical modifications have been explored for establishing structure–property-performance relationship for Y6-based NF-SMAs. In this work, we explored the isomerization on asymmetrical Y6 derivatives by varying the position of alkoxy side chain on the thiophene linkage between the core and one of the end groups of Y6. The isomers with differences in conformational restriction raised by noncovalent interactions as well as steric hindrance revealed distinctive behavior in crystallization and polymorphism, which led to a significant contrast in PSC performances. Here the X-TO1 molecule with alkoxy side chain facing the end group (outward) displayed preferred molecular configuration and polymorph, delivering power conversion efficiency (PCE) of 15.63%, while its isomer X-TO2 showed coexisted polymorphs significantly increased the charge recombination in the PSC devices led to a low PCE around 3%. This structure–property-performance relationship not only highlighted the elegancy of isomerization in tuning the photovoltaic performances but also identified polymorphism as one of the causes for impairing photovoltaic performances of PSCs.},
doi = {10.1016/j.cej.2022.136058},
journal = {Chemical Engineering Journal},
number = ,
volume = 441,
place = {United States},
year = {Mon Mar 28 00:00:00 EDT 2022},
month = {Mon Mar 28 00:00:00 EDT 2022}
}
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Works referenced in this record:
High-Efficiency Thermal-Annealing-Free Organic Solar Cells Based on an Asymmetric Acceptor with Improved Thermal and Air Stability
journal, December 2020
- Zhang, Jinsheng; Han, Yufang; Zhang, Wenxia
- ACS Applied Materials & Interfaces, Vol. 12, Issue 51
Unveiling structure-performance relationships from multi-scales in non-fullerene organic photovoltaics
journal, July 2021
- Li, Shuixing; Zhan, Lingling; Yao, Nannan
- Nature Communications, Vol. 12, Issue 1
Significant Influence of the Methoxyl Substitution Position on Optoelectronic Properties and Molecular Packing of Small-Molecule Electron Acceptors for Photovoltaic Cells
journal, May 2017
- Li, Sunsun; Ye, Long; Zhao, Wenchao
- Advanced Energy Materials, Vol. 7, Issue 17
An asymmetric small molecule acceptor for organic solar cells with a short circuit current density over 24 mA cm−2
journal, January 2020
- Cai, Fangfang; Peng, Hongjian; Chen, Honggang
- Journal of Materials Chemistry A, Vol. 8, Issue 31
Ideal alloys of two donor isomers with non-covalently conformational locking for ternary organic solar cells
journal, January 2020
- Deng, Dan; Zhang, Hao; Wu, Qiong
- Journal of Materials Chemistry C, Vol. 8, Issue 22
Significantly improving the performance of polymer solar cells by the isomeric ending-group based small molecular acceptors: Insight into the isomerization
journal, December 2019
- Luo, Zhenghui; Liu, Tao; Xiao, Yiqun
- Nano Energy, Vol. 66
Over 14.5% efficiency and 71.6% fill factor of ternary organic solar cells with 300 nm thick active layers
journal, January 2020
- Gao, Jinhua; Gao, Wei; Ma, Xiaoling
- Energy & Environmental Science, Vol. 13, Issue 3
Non-fullerene acceptors for organic solar cells
journal, February 2018
- Yan, Cenqi; Barlow, Stephen; Wang, Zhaohui
- Nature Reviews Materials, Vol. 3, Issue 3
Asymmetric Isomer Effects in Benzo[ c ][1,2,5]thiadiazole‐Fused Nonacyclic Acceptors: Dielectric Constant and Molecular Crystallinity Control for Significant Photovoltaic Performance Enhancement
journal, June 2021
- Gao, Wei; Fan, Baobing; Qi, Feng
- Advanced Functional Materials, Vol. 31, Issue 37
Effect of Isomerization on High-Performance Nonfullerene Electron Acceptors
journal, June 2018
- Wang, Jiayu; Zhang, Junxiang; Xiao, Yiqun
- Journal of the American Chemical Society, Vol. 140, Issue 29
A-DA′D-A non-fullerene acceptors for high-performance organic solar cells
journal, July 2020
- Wei, Qingya; Liu, Wei; Leclerc, Mario
- Science China Chemistry, Vol. 63, Issue 10
Asymmetric Alkoxy and Alkyl Substitution on Nonfullerene Acceptors Enabling High‐Performance Organic Solar Cells
journal, November 2020
- Chen, Yuzhong; Bai, Fujin; Peng, Zhengxing
- Advanced Energy Materials, Vol. 11, Issue 3
Charge carrier traps in organic semiconductors: a review on the underlying physics and impact on electronic devices
journal, January 2020
- Haneef, Hamna F.; Zeidell, Andrew M.; Jurchescu, Oana D.
- Journal of Materials Chemistry C, Vol. 8, Issue 3
High‐Efficiency As‐Cast Organic Solar Cells Based on Acceptors with Steric Hindrance Induced Planar Terminal Group
journal, July 2019
- Liu, Yahui; Li, Miao; Yang, Jinjin
- Advanced Energy Materials, Vol. 9, Issue 32
Asymmetrically noncovalently fused-ring acceptor for high-efficiency organic solar cells with reduced voltage loss and excellent thermal stability
journal, August 2020
- Guo, Qing; Lin, Ji; Liu, Haiqin
- Nano Energy, Vol. 74
Preparation of non-fullerene acceptors with a multi-asymmetric configuration in a one-pot reaction for organic solar cells
journal, January 2020
- Zhang, Yi; Wang, Yan; Xie, Ziyi
- Journal of Materials Chemistry C, Vol. 8, Issue 48
Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core
journal, April 2019
- Yuan, Jun; Zhang, Yunqiang; Zhou, Liuyang
- Joule, Vol. 3, Issue 4
Critical review of the molecular design progress in non-fullerene electron acceptors towards commercially viable organic solar cells
journal, January 2019
- Wadsworth, Andrew; Moser, Maximilian; Marks, Adam
- Chemical Society Reviews, Vol. 48, Issue 6
Side-Chain Isomerization on an n-type Organic Semiconductor ITIC Acceptor Makes 11.77% High Efficiency Polymer Solar Cells
journal, November 2016
- Yang, Yankang; Zhang, Zhi-Guo; Bin, Haijun
- Journal of the American Chemical Society, Vol. 138, Issue 45
Fluorinating π‐Extended Molecular Acceptors Yields Highly Connected Crystal Structures and Low Reorganization Energies for Efficient Solar Cells
journal, May 2020
- Swick, Steven M.; Alzola, Joaquin M.; Sangwan, Vinod K.
- Advanced Energy Materials, Vol. 10, Issue 23
Photovoltaic Performances of Fused Ring Acceptors with Isomerized Ladder-Type Dipyran Cores
journal, January 2020
- Li, Miao; Liu, Yahui; Zhou, Yuanyuan
- ACS Applied Materials & Interfaces, Vol. 12, Issue 4
Exploiting Ternary Blends for Improved Photostability in High-Efficiency Organic Solar Cells
journal, March 2020
- Gasparini, Nicola; Paleti, Sri Harish Kumar; Bertrandie, Jules
- ACS Energy Letters, Vol. 5, Issue 5
Enhancing the Photovoltaic Performance of a Benzo[c][1,2,5]thiadiazole-Based Polymer Donor via a Non-Fullerene Acceptor Pairing Strategy
journal, November 2020
- Feng, Shiyu; Lu, Hao; Liu, Yahui
- ACS Applied Materials & Interfaces, Vol. 12, Issue 47
Polymorphism in Non‐Fullerene Acceptors Based on Indacenodithienothiophene
journal, May 2021
- Marina, Sara; Scaccabarozzi, Alberto D.; Gutierrez‐Fernandez, Edgar
- Advanced Functional Materials, Vol. 31, Issue 29
Positional Effect of the 2-Ethylhexyl Carboxylate Side Chain on the Thiophene π-Bridge of Nonfullerene Acceptors for Efficient Organic Solar Cells
journal, October 2021
- Raju, Telugu Bhim; Cho, Hye Won; Gopikrishna, Peddaboodi
- ACS Applied Energy Materials, Vol. 4, Issue 10
High‐Efficiency Organic Solar Cells Based on Asymmetric Acceptors Bearing One 3D Shape‐Persistent Terminal Group
journal, June 2021
- Lu, Hao; Jin, Hui; Huang, Hao
- Advanced Functional Materials, Vol. 31, Issue 35
Highly Efficient Non-Fused-Ring Electron Acceptors Enabled by the Conformational Lock and Structural Isomerization Effects
journal, May 2021
- Zhao, Jun; Xu, Xiaopeng; Yu, Liyang
- ACS Applied Materials & Interfaces, Vol. 13, Issue 21
Conformation Locking of Simple Nonfused Electron Acceptors Via Multiple Intramolecular Noncovalent Bonds to Improve the Performances of Organic Solar Cells
journal, December 2020
- Yao, Zhenghui; Li, Yaokai; Li, Shuixing
- ACS Applied Energy Materials, Vol. 4, Issue 1
Fused-Ring Acceptors with Asymmetric Side Chains for High-Performance Thick-Film Organic Solar Cells
journal, September 2017
- Feng, Shiyu; Zhang, Cai'e; Liu, Yahui
- Advanced Materials, Vol. 29, Issue 42
Effects of polymorphism on charge transport in organic semiconductors
journal, August 2009
- Jurchescu, Oana D.; Mourey, Devin A.; Subramanian, Sankar
- Physical Review B, Vol. 80, Issue 8
A Noncovalently
Fused‐Ring
Asymmetric Electron Acceptor Enables Efficient Organic Solar Cells
journal, July 2021
- Lin, Ji; Guo, Qing; Liu, Qi
- Chinese Journal of Chemistry, Vol. 39, Issue 10
Which isomer is better for charge transport: anti- or syn-?
journal, January 2019
- Hu, Peng; Ye, Jun; Jiang, Hui
- Journal of Materials Chemistry C, Vol. 7, Issue 20
Low-Bandgap Non-fullerene Acceptors Enabling High-Performance Organic Solar Cells
journal, January 2021
- Liu, Wei; Xu, Xiang; Yuan, Jun
- ACS Energy Letters, Vol. 6, Issue 2
Effects of fused-ring regiochemistry on the properties and photovoltaic performance of n-type organic semiconductor acceptors
journal, January 2018
- Li, Xiaojun; Huang, He; Peng, Zhengxing
- Journal of Materials Chemistry A, Vol. 6, Issue 33
Fine-Tuning the Dipole Moment of Asymmetric Non-Fullerene Acceptors Enabling Efficient and Stable Organic Solar Cells
journal, May 2021
- Xia, Zihao; Zhang, Jinsheng; Gao, Xiang
- ACS Applied Materials & Interfaces, Vol. 13, Issue 20
Fine regulation of crystallisation tendency to optimize the BHJ nanostructure and performance of polymer solar cells
journal, January 2020
- Deng, Min; Xu, Xiaopeng; Lee, Young Woong
- Nanoscale, Vol. 12, Issue 24
A Study of Equilibrium Melting of Polyethylene
journal, September 1977
- Wunderlich, Bernhard; Czornyj, George
- Macromolecules, Vol. 10, Issue 5
Side‐Chain Engineering on Y‐Series Acceptors with Chlorinated End Groups Enables High‐Performance Organic Solar Cells
journal, April 2021
- Chen, Yuzhong; Ma, Ruijie; Liu, Tao
- Advanced Energy Materials, Vol. 11, Issue 20
Noncovalently Fused-Ring Electron Acceptors with C 2 v Symmetry for Regulating the Morphology of Organic Solar Cells
journal, September 2020
- Hou, Ran; Li, Miao; Ma, Xueqing
- ACS Applied Materials & Interfaces, Vol. 12, Issue 41
Asymmetric Acceptors Enabling Organic Solar Cells to Achieve an over 17% Efficiency: Conformation Effects on Regulating Molecular Properties and Suppressing Nonradiative Energy Loss
journal, December 2020
- Gao, Wei; Fu, Huiting; Li, Yuxiang
- Advanced Energy Materials, Vol. 11, Issue 4
Fine-Tuning Energy Levels via Asymmetric End Groups Enables Polymer Solar Cells with Efficiencies over 17%
journal, June 2020
- Luo, Zhenghui; Ma, Ruijie; Liu, Tao
- Joule, Vol. 4, Issue 6
Dithienogermole-Based Nonfullerene Acceptors: Roles of the Side-Chains’ Direction and Development of Green-Tinted Efficient Semitransparent Organic Solar Cells
journal, June 2020
- Cho, Yongjoon; Lee, Tack Ho; Jeong, Seonghun
- ACS Applied Energy Materials, Vol. 3, Issue 8
Asymmetric Electron Acceptors for High‐Efficiency and Low‐Energy‐Loss Organic Photovoltaics
journal, May 2020
- Li, Shuixing; Zhan, Lingling; Jin, Yingzhi
- Advanced Materials, Vol. 32, Issue 24