Chalcogen effect on the photovoltaic performance of nonfused-ring small molecular electron acceptors for efficient organic solar cells

Liu, Siyang; Chen, Xiaowei; Li, Yinfeng; Xu, Xiaopeng; Yu, Liyang; Duan, Yuwei; Li, Ruipeng; Peng, Qiang

doi:10.1016/j.cej.2024.150579

Title: Chalcogen effect on the photovoltaic performance of nonfused-ring small molecular electron acceptors for efficient organic solar cells

Journal Article · 19 March 2024 · Chemical Engineering Journal

DOI: https://doi.org/10.1016/j.cej.2024.150579 · OSTI ID:2440570

Liu, Siyang ^[1]; Chen, Xiaowei ^[1]; Li, Yinfeng ^[1]; Xu, Xiaopeng ^[1];

^[1]; Duan, Yuwei ^[2]; Li, Ruipeng ^[3];

^[4]

Sichuan Univ., Chengdu (China)
Chengdu University of Technology (China)
Brookhaven National Laboratory (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)
Sichuan Univ., Chengdu (China); Chengdu University of Technology (China)

Fused-ring electron acceptors (FREAs) are the current working horse for the top performing organic solar cells (OSCs). Nevertheless, these FREAs surfer from high synthetic complexity, production costs and poor scalability, hindering their industrialization. Developing nonfused-ring electron acceptors (NFREAs) is a more feasible alternative solution towards future photovoltaic applications. Here, in this work, a series of NFREAs have been designed and synthesized by introducing chalcogen atoms on the side chains for OSCs. The introduced chalcogen atoms (O, S, and Se) not only modulated the energy levels but also finely tuned the intermolecular interactions. Especially, the formed S···S and Se···Se intermolecular interactions in TTS-4F and TTSe-4F resulted in higher molecular crystallinity than TTO-4F. Unexpectedly, the strong Se···Se interactions also led the aggregation of TTSe-4F and formation of large domains in the PM6:TTSe-4F blend. The moderate S···S interactions in TTS-4F enabled an optimal phase separation with more ideal nano fibrils distributed in the PM6:TTS-4F blend, facilitating the charge separation and transport. As a result, TTS-4F based devices achieved a champion power conversion efficiency (PCE) of 14.74%, higher than the TTO-4F (8.76%) and TTSe-4F (11.56%) based devices.

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012704

OSTI ID:: 2440570

Report Number(s):: BNL--226012-2024-JAAM

Journal Information:: Chemical Engineering Journal, Journal Name: Chemical Engineering Journal Vol. 487; ISSN 1385-8947

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (36)

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
Sequential Deposition of Multicomponent Bulk Heterojunctions Increases Efficiency of Organic Solar Cells Xu, Xiaopeng; Jing, Wenwen; Meng, Huifeng Advanced Materials, Vol. 35, Issue 12 https://doi.org/10.1002/adma.202208997	journal	February 2023
18.6% Efficiency All‐Polymer Solar Cells Enabled by a Wide Bandgap Polymer Donor Based on Benzo[1,2‐d:4,5‐d′]bisthiazole Wu, Peixi; Duan, Yuwei; Li, Yinfeng Advanced Materials, Vol. 36, Issue 3 https://doi.org/10.1002/adma.202306990	journal	December 2023
High‐Efficiency As‐Cast Organic Solar Cells Based on Acceptors with Steric Hindrance Induced Planar Terminal Group Liu, Yahui; Li, Miao; Yang, Jinjin Advanced Energy Materials, Vol. 9, Issue 32 https://doi.org/10.1002/aenm.201901280	journal	July 2019
Recent progress in low‐cost noncovalently fused‐ring electron acceptors for organic solar cells Bai, Qingqing; Liang, Qiming; Li, Henan Aggregate, Vol. 3, Issue 6 https://doi.org/10.1002/agt2.281	journal	October 2022
A Fully Non‐fused Ring Acceptor with Planar Backbone and Near‐IR Absorption for High Performance Polymer Solar Cells Chen, Ya‐Nan; Li, Miao; Wang, Yunzhi Angewandte Chemie International Edition, Vol. 59, Issue 50 https://doi.org/10.1002/anie.202010856	journal	October 2020
Simple Non‐Fused Electron Acceptors Leading to Efficient Organic Photovoltaics Wen, Tian‐Jiao; Liu, Zhi‐Xi; Chen, Zeng Angewandte Chemie International Edition, Vol. 60, Issue 23 https://doi.org/10.1002/anie.202101867	journal	May 2021
A Synergistic Strategy of Manipulating the Number of Selenophene Units and Dissymmetric Central Core of Small Molecular Acceptors Enables Polymer Solar Cells with 17.5 % Efficiency Yang, Can; An, Qiaoshi; Bai, Hai‐Rui Angewandte Chemie International Edition, Vol. 60, Issue 35 https://doi.org/10.1002/anie.202104766	journal	July 2021
Design of a Fully Non‐Fused Bulk Heterojunction toward Efficient and Low‐Cost Organic Photovoltaics Ma, Lijiao; Zhang, Shaoqing; Ren, Junzhen Angewandte Chemie International Edition, Vol. 62, Issue 5 https://doi.org/10.1002/anie.202214088	journal	December 2022
Harnessing the Structure‐Performance Relationships in Designing Non‐Fused Ring Acceptors for Organic Solar Cells Mishra, Amaresh; Sharma, Ganesh D. Angewandte Chemie International Edition, Vol. 62, Issue 21 https://doi.org/10.1002/anie.202219245	journal	March 2023
Molecular Insights of Non‐fused Ring Acceptors for High‐Performance Non‐fullerene Organic Solar Cells Li, Yibin; Yu, Jiangsheng; Zhou, Yinhua Chemistry – A European Journal, Vol. 28, Issue 57 https://doi.org/10.1002/chem.202201675	journal	August 2022
Design and Synthesis of N‐Alkylaniline‐Substituted Low Band‐Gap Electron Acceptors for Photovoltaic Application Li, Jiayao; Li, Hao; Ma, Lijiao Chinese Journal of Chemistry, Vol. 41, Issue 4 https://doi.org/10.1002/cjoc.202200579	journal	December 2022
A Simple Building Block with Noncovalently Conformational Locks towards Constructing Low-Cost and High-Performance Nonfused Ring Electron Acceptors Gu, Xiao-Bin; Gao, Jin-Hua; Han, Zi-Yang Chinese Journal of Polymer Science, Vol. 41, Issue 4 https://doi.org/10.1007/s10118-022-2888-9	journal	November 2022
Asymmetric simple unfused acceptor enabling over 12% efficiency organic solar cells Cao, Jinru; Qu, Shenya; Yang, Linqiang Chemical Engineering Journal, Vol. 412 https://doi.org/10.1016/j.cej.2021.128770	journal	May 2021
High-performance and low-energy loss organic solar cells with non-fused ring acceptor by alkyl chain engineering Luo, Dou; Lai, Xue; Zheng, Nan Chemical Engineering Journal, Vol. 420 https://doi.org/10.1016/j.cej.2021.129768	journal	September 2021
High efficiency ternary organic solar cells via morphology regulation with asymmetric nonfused ring electron acceptor Li, Miao; Feng, Shiyu; Shen, Shuaishuai Chemical Engineering Journal, Vol. 438 https://doi.org/10.1016/j.cej.2022.135384	journal	June 2022
A simple high-performance fully nonfused ring electron acceptor with a planar molecular backbone Zheng, Xinming; Liu, Wenlong; Lu, Hao Chemical Engineering Journal, Vol. 444 https://doi.org/10.1016/j.cej.2022.136472	journal	September 2022
Progressive evolutions of non-fused ring electron acceptors toward efficient organic solar cells with improved photocurrent and reduced energy loss Shen, Qing; He, Chengliang; Wu, Baohua Chemical Engineering Journal, Vol. 471 https://doi.org/10.1016/j.cej.2023.144472	journal	September 2023
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
Selenium-Containing Organic Photovoltaic Materials Fan, Baobing; Lin, Francis; Wu, Xin Accounts of Chemical Research, Vol. 54, Issue 20 https://doi.org/10.1021/acs.accounts.1c00443	journal	October 2021
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
Designing High-Performance Nonfused Ring Electron Acceptors via Synergistically Adjusting Side Chains and Electron-Withdrawing End-Groups Zhang, Yan; Zhang, Cai’e; Zhang, Andong ACS Applied Materials & Interfaces, Vol. 14, Issue 18 https://doi.org/10.1021/acsami.2c01190	journal	April 2022
Simple-Structured NIR-Absorbing Small-Molecule Acceptors with a Thiazolothiazole Core: Multiple Noncovalent Conformational Locks and D–A Effect for Efficient OSCs Peng, Wenhong; Zhang, Guangjun; Zhu, Mengbing ACS Applied Materials & Interfaces, Vol. 11, Issue 51 https://doi.org/10.1021/acsami.9b16686	journal	November 2019
Over 17% Efficiency Binary Organic Solar Cells with Photoresponses Reaching 1000 nm Enabled by Selenophene-Fused Nonfullerene Acceptors Qi, Feng; Jiang, Kui; Lin, Francis ACS Energy Letters, Vol. 6, Issue 1 https://doi.org/10.1021/acsenergylett.0c02230	journal	November 2020
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
Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells Huang, Hao; Guo, Qingxin; Feng, Shiyu Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-11001-6	journal	July 2019
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
Precise synthesis and photovoltaic properties of giant molecule acceptors Zhuo, Hongmei; Li, Xiaojun; Zhang, Jinyuan Nature Communications, Vol. 14, Issue 1 https://doi.org/10.1038/s41467-023-43846-3	journal	December 2023
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
Single-junction organic solar cells with over 19% efficiency enabled by a refined double-fibril network morphology Zhu, Lei; Zhang, Ming; Xu, Jinqiu Nature Materials, Vol. 21, Issue 6 https://doi.org/10.1038/s41563-022-01244-y	journal	May 2022
Advantages, challenges and molecular design of different material types used in organic solar cells Yi, Jicheng; Zhang, Guangye; Yu, Han Nature Reviews Materials, Vol. 9, Issue 1 https://doi.org/10.1038/s41578-023-00618-1	journal	December 2023
Alkoxythiophene and alkylthiothiophene π-bridges enhance the performance of A–D–A electron acceptors Zhang, Lei; Jin, Ke; Xiao, Zuo Materials Chemistry Frontiers, Vol. 3, Issue 3 https://doi.org/10.1039/C8QM00647D	journal	January 2019
Highly efficient near-infrared and semitransparent polymer solar cells based on an ultra-narrow bandgap nonfullerene acceptor Chen, Juan; Li, Guangda; Zhu, Qinglian Journal of Materials Chemistry A, Vol. 7, Issue 8 https://doi.org/10.1039/C8TA11484F	journal	January 2019
Achieving high-performance non-halogenated nonfullerene acceptor-based organic solar cells with 13.7% efficiency via a synergistic strategy of an indacenodithieno[3,2- b ]selenophene core unit and non-halogenated thiophene-based terminal group Liu, Kai-Kai; Xu, Xiaopeng; Wang, Jin-Liang Journal of Materials Chemistry A, Vol. 7, Issue 42 https://doi.org/10.1039/C9TA08328F	journal	January 2019
Alkoxy substitution on IDT-Series and Y-Series non-fullerene acceptors yielding highly efficient organic solar cells Chen, Yuzhong; Liu, Tao; Ma, Lik-Kuen Journal of Materials Chemistry A, Vol. 9, Issue 12 https://doi.org/10.1039/D0TA10953C	journal	January 2021

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36 MATERIALS SCIENCE
Chalcogen atom substitution
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Organic solar cells
Power conversion efficiency
Side chain engineering

Title: Chalcogen effect on the photovoltaic performance of nonfused-ring small molecular electron acceptors for efficient organic solar cells

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