Lowly Fused Non-Fullerene Acceptors Towards Efficient Organic Solar Cells Enabled by Isomerization

Deng, Min; Xu, Xiao-Peng; Yu, Li-Yang; Li, Rui-Peng; Peng, Qiang

doi:10.1007/s10118-022-2751-z

Lowly Fused Non-Fullerene Acceptors Towards Efficient Organic Solar Cells Enabled by Isomerization

Journal Article · Wed Jun 22 00:00:00 EDT 2022 · Chinese Journal of Polymer Science

DOI:https://doi.org/10.1007/s10118-022-2751-z· OSTI ID:1890202

Deng, Min ^[1]; Xu, Xiao-Peng ^[1]; Yu, Li-Yang ^[1]; Li, Rui-Peng ^[2]; Peng, Qiang ^[1]

Sichuan Univ., Chengdu (China)
Brookhaven National Lab. (BNL), Upton, NY (United States)

Here two lowly fused non-fullerene acceptors (NFAs) with isomeric structures, named as BTP-out-4F and BTP-in-4F, were developed by tailoring the fused 7-ring central core of Y6 into a lowly fused 5-ring linked with two octyloxythiophene bridges. BTP-out-4F with octyloxy side chains away from the central core exhibited large steric hindrance that restrained the rotational freedom between the thiophene bridge and end group but maintained free rotation between the central core and the thiophene bridge. In contrast, BTP-in-4F with octyloxy side chains close to the central core had much lower rotation freedom due to the non-covalent S^…O interactions locked the central core, thiophene bridge and end group simultaneously, making BTP-in-4F have higher molecular crystallinity. On the other hand, the optical properties, energy levels and the blend morphology properties were significantly influenced, leading to distinctive photovoltaic performances. BTP-out-4F formed favorable energy level alignment and morphology when matching with PBDB-T donor, thus its device realized a much higher PCE of 13.32%, which was over 13 times than that of BTP-in-4F based device (PCE=0.97%).

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: Foundation of State Key Laboratory of Polymer Materials Engineering; Fundamental Research Funds for the Central Universities; National Natural Science Foundation of China (NSFC); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012704

OSTI ID:: 1890202

Report Number(s):: BNL-223510-2022-JAAM

Journal Information:: Chinese Journal of Polymer Science, Journal Name: Chinese Journal of Polymer Science Journal Issue: 8 Vol. 40; ISSN 0256-7679

Publisher:: Springer NatureCopyright Statement

Country of Publication:: United States

Language:: English

References (43)

Wide Bandgap Molecular Acceptors with a Truxene Core for Efficient Nonfullerene Polymer Solar Cells: Linkage Position on Molecular Configuration and Photovoltaic Properties Wu, Wenlin; Zhang, Guangjun; Xu, Xiaopeng Advanced Functional Materials, Vol. 28, Issue 18 https://doi.org/10.1002/adfm.201707493	journal	March 2018
Isomerization Strategy of Nonfullerene Small‐Molecule Acceptors for Organic Solar Cells Luo, Zhenghui; Liu, Tao; Yan, He Advanced Functional Materials, Vol. 30, Issue 46 https://doi.org/10.1002/adfm.202004477	journal	September 2020
Polymer Solar Cells with 18.74% Efficiency: From Bulk Heterojunction to Interdigitated Bulk Heterojunction Xu, Xiaopeng; Yu, Liyang; Meng, Huifeng Advanced Functional Materials, Vol. 32, Issue 4 https://doi.org/10.1002/adfm.202108797	journal	October 2021
Simple Nonfused‐Ring Electron Acceptors with Noncovalently Conformational Locks for Low‐Cost and High‐Performance Organic Solar Cells Enabled by End‐Group Engineering Li, Congqi; Zhang, Xin; Yu, Na Advanced Functional Materials, Vol. 32, Issue 5 https://doi.org/10.1002/adfm.202108861	journal	October 2021
An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells Lin, Yuze; Wang, Jiayu; Zhang, Zhi-Guo Advanced Materials, Vol. 27, Issue 7 https://doi.org/10.1002/adma.201404317	journal	January 2015
Design and Synthesis of a Low Bandgap Small Molecule Acceptor for Efficient Polymer Solar Cells Yao, Huifeng; Chen, Yu; Qin, Yunpeng Advanced Materials, Vol. 28, Issue 37 https://doi.org/10.1002/adma.201602642	journal	July 2016
Single‐Junction Organic Photovoltaic Cells with Approaching 18% Efficiency Cui, Yong; Yao, Huifeng; Zhang, Jianqi Advanced Materials, Vol. 32, Issue 19 https://doi.org/10.1002/adma.201908205	journal	March 2020
Asymmetric Electron Acceptors for High‐Efficiency and Low‐Energy‐Loss Organic Photovoltaics Li, Shuixing; Zhan, Lingling; Jin, Yingzhi Advanced Materials, Vol. 32, Issue 24 https://doi.org/10.1002/adma.202001160	journal	May 2020
Single‐Junction Organic Photovoltaic Cell with 19% Efficiency Cui, Yong; Xu, Ye; Yao, Huifeng Advanced Materials, Vol. 33, Issue 41 https://doi.org/10.1002/adma.202102420	journal	August 2021
Realizing 19.05% Efficiency Polymer Solar Cells by Progressively Improving Charge Extraction and Suppressing Charge Recombination Chong, Kaien; Xu, Xiaopeng; Meng, Huifeng Advanced Materials, Vol. 34, Issue 13 https://doi.org/10.1002/adma.202109516	journal	February 2022
Asymmetric Acceptors Enabling Organic Solar Cells to Achieve an over 17% Efficiency: Conformation Effects on Regulating Molecular Properties and Suppressing Nonradiative Energy Loss Gao, Wei; Fu, Huiting; Li, Yuxiang Advanced Energy Materials, Vol. 11, Issue 4 https://doi.org/10.1002/aenm.202003177	journal	December 2020
Side‐Chain Engineering on Y‐Series Acceptors with Chlorinated End Groups Enables High‐Performance Organic Solar Cells Chen, Yuzhong; Ma, Ruijie; Liu, Tao Advanced Energy Materials, Vol. 11, Issue 20 https://doi.org/10.1002/aenm.202003777	journal	April 2021
Replacing Alkoxy Groups with Alkylthienyl Groups: A Feasible Approach To Improve the Properties of Photovoltaic Polymers Huo, Lijun; Zhang, Shaoqing; Guo, Xia Angewandte Chemie International Edition, Vol. 50, Issue 41 https://doi.org/10.1002/anie.201103313	journal	August 2011
Tuning the Hybridization of Local Exciton and Charge‐Transfer States in Highly Efficient Organic Photovoltaic Cells Xu, Ye; Yao, Huifeng; Ma, Lijiao Angewandte Chemie International Edition, Vol. 59, Issue 23 https://doi.org/10.1002/anie.201915030	journal	March 2020
18.77 % Efficiency Organic Solar Cells Promoted by Aqueous Solution Processed Cobalt(II) Acetate Hole Transporting Layer Meng, Huifeng; Liao, Chentong; Deng, Min Angewandte Chemie International Edition, Vol. 60, Issue 41 https://doi.org/10.1002/anie.202110550	journal	September 2021
Non‐Fused Polymerized Small Molecular Acceptors for Efficient All‐Polymer Solar Cells Wu, Baoqi; Zhang, Yue; Tian, Shizeng Solar RRL, Vol. 6, Issue 6 https://doi.org/10.1002/solr.202101034	journal	March 2022
Tuning the intermolecular interaction of A2-A1-D-A1-A2 type non-fullerene acceptors by substituent engineering for organic solar cells with ultrahigh VOC of ~1.2 V Wang, Xiaochen; Tang, Ailing; Yang, Jing Science China Chemistry, Vol. 63, Issue 11 https://doi.org/10.1007/s11426-020-9840-x	journal	September 2020
Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core Yuan, Jun; Zhang, Yunqiang; Zhou, Liuyang Joule, Vol. 3, Issue 4 https://doi.org/10.1016/j.joule.2019.01.004	journal	April 2019
Efficient Organic Solar Cells from Molecular Orientation Control of M-Series Acceptors Ma, Yunlong; Zhang, Ming; Wan, Shuo Joule, Vol. 5, Issue 1 https://doi.org/10.1016/j.joule.2020.11.006	journal	January 2021
Enhancing the Performance of Organic Solar Cells by Hierarchically Supramolecular Self-Assembly of Fused-Ring Electron Acceptors Liu, Yahui; Zhang, Cai’e; Hao, Dan Chemistry of Materials, Vol. 30, Issue 13 https://doi.org/10.1021/acs.chemmater.8b01319	journal	June 2018
Benzotriazole-Based Acceptor and Donors, Coupled with Chlorination, Achieve a High V _OC of 1.24 V and an Efficiency of 10.5% in Fullerene-Free Organic Solar Cells Tang, Ailing; Song, Wei; Xiao, Bo Chemistry of Materials, Vol. 31, Issue 11 https://doi.org/10.1021/acs.chemmater.8b05316	journal	May 2019
Nonfused Nonfullerene Acceptors with an A–D–A′–D–A Framework and a Benzothiadiazole Core for High-Performance Organic Solar Cells Pang, Shuting; Zhou, Xia; Zhang, Song ACS Applied Materials & Interfaces, Vol. 12, Issue 14 https://doi.org/10.1021/acsami.0c01850	journal	March 2020
Noncovalently Fused-Ring Electron Acceptors with C _{2 v} Symmetry for Regulating the Morphology of Organic Solar Cells Hou, Ran; Li, Miao; Ma, Xueqing ACS Applied Materials & Interfaces, Vol. 12, Issue 41 https://doi.org/10.1021/acsami.0c13993	journal	September 2020
Highly Efficient Nonfullerene Acceptor with Sulfonyl-Based Ending Groups Tao, Lupiao; Liu, Xiaohui; Deng, Changbo ACS Applied Materials & Interfaces, Vol. 12, Issue 44 https://doi.org/10.1021/acsami.0c14774	journal	October 2020
Highly Efficient Non-Fused-Ring Electron Acceptors Enabled by the Conformational Lock and Structural Isomerization Effects Zhao, Jun; Xu, Xiaopeng; Yu, Liyang ACS Applied Materials & Interfaces, Vol. 13, Issue 21 https://doi.org/10.1021/acsami.1c06299	journal	May 2021
End-Group Modifications with Bromine and Methyl in Nonfullerene Acceptors: The Effect of Isomerism Chen, Lin; Cao, Congcong; Lai, Hanjian ACS Applied Materials & Interfaces, Vol. 13, Issue 25 https://doi.org/10.1021/acsami.1c08060	journal	June 2021
Exploiting Ternary Blends for Improved Photostability in High-Efficiency Organic Solar Cells Gasparini, Nicola; Paleti, Sri Harish Kumar; Bertrandie, Jules ACS Energy Letters, Vol. 5, Issue 5 https://doi.org/10.1021/acsenergylett.0c00604	journal	March 2020
A Non-fullerene Acceptor with Enhanced Intermolecular π-Core Interaction for High-Performance Organic Solar Cells Lin, Francis; Jiang, Kui; Kaminsky, Werner Journal of the American Chemical Society, Vol. 142, Issue 36 https://doi.org/10.1021/jacs.0c07083	journal	August 2020
Selenium Heterocyclic Electron Acceptor with Small Urbach Energy for As-Cast High-Performance Organic Solar Cells Zhang, Zhenzhen; Li, Yawen; Cai, Guilong Journal of the American Chemical Society, Vol. 142, Issue 44 https://doi.org/10.1021/jacs.0c08557	journal	October 2020
Improved Light Harvesting and Improved Efficiency by Insertion of an Optical Spacer (ZnO) in Solution-Processed Small-Molecule Solar Cells Kyaw, Aung Ko Ko; Wang, Dong Hwan; Wynands, David Nano Letters, Vol. 13, Issue 8 https://doi.org/10.1021/nl401758g	journal	July 2013
Organic solar cells based on non-fullerene acceptors Hou, Jianhui; Inganäs, Olle; Friend, Richard H. Nature Materials, Vol. 17, Issue 2 https://doi.org/10.1038/nmat5063	journal	January 2018
Simple non-fused electron acceptors for efficient and stable organic solar cells Yu, Zhi-Peng; Liu, Zhi-Xi; Chen, Fang-Xiao Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10098-z	journal	May 2019
Over 16% efficiency organic photovoltaic cells enabled by a chlorinated acceptor with increased open-circuit voltages Cui, Yong; Yao, Huifeng; Zhang, Jianqi Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10351-5	journal	June 2019
Graded bulk-heterojunction enables 17% binary organic solar cells via nonhalogenated open air coating Zhang, Ying; Liu, Kuan; Huang, Jiaming Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-25148-8	journal	August 2021
Completely non-fused electron acceptor with 3D-interpenetrated crystalline structure enables efficient and stable organic solar cell Ma, Lijiao; Zhang, Shaoqing; Zhu, Jincheng Nature Communications, Vol. 12, Issue 1 https://doi.org/10.1038/s41467-021-25394-w	journal	August 2021
Non-fullerene acceptors with branched side chains and improved molecular packing to exceed 18% efficiency in organic solar cells Li, Chao; Zhou, Jiadong; Song, Jiali Nature Energy, Vol. 6, Issue 6 https://doi.org/10.1038/s41560-021-00820-x	journal	May 2021
High-performance fullerene-free polymer solar cells with 6.31% efficiency Lin, Yuze; Zhang, Zhi-Guo; Bai, Huitao Energy & Environmental Science, Vol. 8, Issue 2 https://doi.org/10.1039/C4EE03424D	journal	January 2015
Revealing the effects of molecular packing on the performances of polymer solar cells based on A–D–C–D–A type non-fullerene acceptors Li, Shuixing; Zhan, Lingling; Zhao, Wenchao Journal of Materials Chemistry A, Vol. 6, Issue 25 https://doi.org/10.1039/C8TA03753A	journal	January 2018
Tuning the electron-deficient core of a non-fullerene acceptor to achieve over 17% efficiency in a single-junction organic solar cell Zhu, Can; Yuan, Jun; Cai, Fangfang Energy & Environmental Science, Vol. 13, Issue 8 https://doi.org/10.1039/D0EE00862A	journal	January 2020
Effect of the chlorine substitution position of the end-group on intermolecular interactions and photovoltaic performance of small molecule acceptors Li, Xiaojun; Angunawela, Indunil; Chang, Yuan Energy & Environmental Science, Vol. 13, Issue 12 https://doi.org/10.1039/D0EE02251A	journal	January 2020
Fine-tuning of side-chain orientations on nonfullerene acceptors enables organic solar cells with 17.7% efficiency Chai, Gaoda; Chang, Yuan; Zhang, Jianquan Energy & Environmental Science, Vol. 14, Issue 6 https://doi.org/10.1039/D0EE03506H	journal	January 2021
Incorporation of alkylthio side chains on benzothiadiazole-based non-fullerene acceptors enables high-performance organic solar cells with over 16% efficiency Cheung, Andy Man Hong; Yu, Han; Luo, Siwei Journal of Materials Chemistry A, Vol. 8, Issue 44 https://doi.org/10.1039/D0TA08830G	journal	January 2020
Non-fused ring acceptors for organic solar cells Yang, Mingqun; Wei, Wenkui; Zhou, Xia Energy Materials, Vol. 1, Issue 1 https://doi.org/10.20517/energymater.2021.08	journal	January 2022

Similar Records

Smartly Optimizing Crystallinity, Compatibility, and Morphology for Polymer Solar Cells by Small Molecule Acceptor with Unique 2D-EDOT Side Chain

Journal Article · Mon Jan 16 19:00:00 EST 2023 · Advanced Functional Materials · OSTI ID:1973506

Y-Type Non-Fullerene Acceptors with Outer Branched Side Chains and Inner Cyclohexane Side Chains for 19.36% Efficiency Polymer Solar Cells

Journal Article · Tue Jan 03 19:00:00 EST 2023 · Advanced Materials · OSTI ID:1974389

Related Subjects

36 MATERIALS SCIENCE
confirmation lock
lowly fused
nonfullerene acceptors
polymer solar cells
structural isomerization

Lowly Fused Non-Fullerene Acceptors Towards Efficient Organic Solar Cells Enabled by Isomerization

Citation Formats

References (43)

Similar Records

Related Subjects