Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells
Abstract
Non-fullerene fused-ring electron acceptors boost the power conversion efficiency of organic solar cells, but they suffer from high synthetic cost and low yield. Here, we show a series of low-cost noncovalently fused-ring electron acceptors, which consist of a ladder-like core locked by noncovalent sulfur–oxygen interactions and flanked by two dicyanoindanone electron-withdrawing groups. Compared with that of similar but unfused acceptor, the presence of ladder-like structure markedly broadens the absorption to the near-infrared region. In addition, the use of intramolecular noncovalent interactions avoids the tedious synthesis of covalently fused-ring structures and markedly lowers the synthetic cost. The optimized solar cells displayed an outstanding efficiency of 13.24%. More importantly, solar cells based on these acceptors demonstrate very low non-radiative energy losses. This research demonstrates that low-cost noncovalently fused-ring electron acceptors are promising to achieve high-efficiency organic solar cells.
- Authors:
-
[4];
- Key Laboratory of Energy Conversion and Storage Materials, College of Chemistry, Beijing Normal University, Beijing, China
- State Key Laboratory for Mechanical Behavior of Materials, Xi’an Jiaotong University, Xi’an, China
- Center for Advanced Low-dimension Materials, State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, China
- Engineering Research Center for Nanomaterials, Henan University, Kaifeng, China
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC)
- OSTI Identifier:
- 1624169
- Grant/Contract Number:
- AC02-05CH11231
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Nature Communications
- Additional Journal Information:
- Journal Volume: 10; Journal Issue: 1; Journal ID: ISSN 2041-1723
- Publisher:
- Nature Publishing Group
- Country of Publication:
- United States
- Language:
- English
- Subject:
- Science & Technology - Other Topics
Citation Formats
Huang, Hao, Guo, Qingxin, Feng, Shiyu, Zhang, Cai’e, Bi, Zhaozhao, Xue, Wenyue, Yang, Jinjin, Song, Jinsheng, Li, Cuihong, Xu, Xinjun, Tang, Zheng, Ma, Wei, and Bo, Zhishan. Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells. United States: N. p., 2019.
Web. doi:10.1038/s41467-019-11001-6.
Huang, Hao, Guo, Qingxin, Feng, Shiyu, Zhang, Cai’e, Bi, Zhaozhao, Xue, Wenyue, Yang, Jinjin, Song, Jinsheng, Li, Cuihong, Xu, Xinjun, Tang, Zheng, Ma, Wei, & Bo, Zhishan. Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells. United States. https://doi.org/10.1038/s41467-019-11001-6
Huang, Hao, Guo, Qingxin, Feng, Shiyu, Zhang, Cai’e, Bi, Zhaozhao, Xue, Wenyue, Yang, Jinjin, Song, Jinsheng, Li, Cuihong, Xu, Xinjun, Tang, Zheng, Ma, Wei, and Bo, Zhishan. Wed .
"Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells". United States. https://doi.org/10.1038/s41467-019-11001-6. https://www.osti.gov/servlets/purl/1624169.
@article{osti_1624169,
title = {Noncovalently fused-ring electron acceptors with near-infrared absorption for high-performance organic solar cells},
author = {Huang, Hao and Guo, Qingxin and Feng, Shiyu and Zhang, Cai’e and Bi, Zhaozhao and Xue, Wenyue and Yang, Jinjin and Song, Jinsheng and Li, Cuihong and Xu, Xinjun and Tang, Zheng and Ma, Wei and Bo, Zhishan},
abstractNote = {Non-fullerene fused-ring electron acceptors boost the power conversion efficiency of organic solar cells, but they suffer from high synthetic cost and low yield. Here, we show a series of low-cost noncovalently fused-ring electron acceptors, which consist of a ladder-like core locked by noncovalent sulfur–oxygen interactions and flanked by two dicyanoindanone electron-withdrawing groups. Compared with that of similar but unfused acceptor, the presence of ladder-like structure markedly broadens the absorption to the near-infrared region. In addition, the use of intramolecular noncovalent interactions avoids the tedious synthesis of covalently fused-ring structures and markedly lowers the synthetic cost. The optimized solar cells displayed an outstanding efficiency of 13.24%. More importantly, solar cells based on these acceptors demonstrate very low non-radiative energy losses. This research demonstrates that low-cost noncovalently fused-ring electron acceptors are promising to achieve high-efficiency organic solar cells.},
doi = {10.1038/s41467-019-11001-6},
journal = {Nature Communications},
number = 1,
volume = 10,
place = {United States},
year = {Wed Jul 10 00:00:00 EDT 2019},
month = {Wed Jul 10 00:00:00 EDT 2019}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
The effect of end-capping groups in A-D-A type non-fullerene acceptors on device performance of organic solar cells
journal, September 2017
- Jia, Jianchao; Zheng, Nannan; Wang, Zhenfeng
- Science China Chemistry, Vol. 60, Issue 11
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
Enhancing Performance of Nonfullerene Acceptors via Side-Chain Conjugation Strategy
journal, July 2017
- Wang, Jiayu; Wang, Wei; Wang, Xiaohui
- Advanced Materials, Vol. 29, Issue 35
An Electron Acceptor with Broad Visible-NIR Absorption and Unique Solid State Packing for As-Cast High Performance Binary Organic Solar Cells
journal, June 2018
- Shi, Xueliang; Liao, Xunfan; Gao, Ke
- Advanced Functional Materials, Vol. 28, Issue 33
A chlorinated low-bandgap small-molecule acceptor for organic solar cells with 14.1% efficiency and low energy loss
journal, July 2018
- Kan, Bin; Feng, Huanran; Yao, Huifeng
- Science China Chemistry, Vol. 61, Issue 10
A Wide Band Gap Polymer with a Deep Highest Occupied Molecular Orbital Level Enables 14.2% Efficiency in Polymer Solar Cells
journal, May 2018
- Li, Sunsun; Ye, Long; Zhao, Wenchao
- Journal of the American Chemical Society, Vol. 140, Issue 23
Design and Synthesis of a Low Bandgap Small Molecule Acceptor for Efficient Polymer Solar Cells
journal, July 2016
- Yao, Huifeng; Chen, Yu; Qin, Yunpeng
- Advanced Materials, Vol. 28, Issue 37
Ternary Nonfullerene Polymer Solar Cells with 12.16% Efficiency by Introducing One Acceptor with Cascading Energy Level and Complementary Absorption
journal, November 2017
- Jiang, Weigang; Yu, Runnan; Liu, Zhiyang
- Advanced Materials, Vol. 30, Issue 1
Effect of Core Size on Performance of Fused-Ring Electron Acceptors
journal, July 2018
- Dai, Shuixing; Xiao, Yiqun; Xue, Peiyao
- Chemistry of Materials, Vol. 30, Issue 15
Naphthodithiophene-Based Nonfullerene Acceptor for High-Performance Organic Photovoltaics: Effect of Extended Conjugation
journal, November 2017
- Zhu, Jingshuai; Ke, Zhifan; Zhang, Qianqian
- Advanced Materials, Vol. 30, Issue 2
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
Dithienopicenocarbazole-Based Acceptors for Efficient Organic Solar Cells with Optoelectronic Response Over 1000 nm and an Extremely Low Energy Loss
journal, February 2018
- Yao, Zhaoyang; Liao, Xunfan; Gao, Ke
- Journal of the American Chemical Society, Vol. 140, Issue 6
Non-fullerene acceptor with low energy loss and high external quantum efficiency: towards high performance polymer solar cells
journal, January 2016
- Li, Yongxi; Liu, Xiaodong; Wu, Fu-Peng
- Journal of Materials Chemistry A, Vol. 4, Issue 16
Fused Nonacyclic Electron Acceptors for Efficient Polymer Solar Cells
journal, January 2017
- Dai, Shuixing; Zhao, Fuwen; Zhang, Qianqian
- Journal of the American Chemical Society, Vol. 139, Issue 3
Ladder-type nonacyclic indacenodithieno[3,2-b]indole for highly efficient organic field-effect transistors and organic photovoltaics
journal, January 2017
- Zhao, Baomin; Yan, Cenqi; Wang, Zheng
- Journal of Materials Chemistry C, Vol. 5, Issue 35
Exploiting Noncovalently Conformational Locking as a Design Strategy for High Performance Fused-Ring Electron Acceptor Used in Polymer Solar Cells
journal, February 2017
- Liu, Yahui; Zhang, Zhe; Feng, Shiyu
- Journal of the American Chemical Society, Vol. 139, Issue 9
An Unfused-Core-Based Nonfullerene Acceptor Enables High-Efficiency Organic Solar Cells with Excellent Morphological Stability at High Temperatures
journal, December 2017
- Li, Shuixing; Zhan, Lingling; Liu, Feng
- Advanced Materials, Vol. 30, Issue 6
Phthalimide-Based Polymers for High Performance Organic Thin-Film Transistors
journal, June 2009
- Guo, Xugang; Kim, Felix Sunjoo; Jenekhe, Samson A.
- Journal of the American Chemical Society, Vol. 131, Issue 21, p. 7206-7207
Dialkoxybithiazole: A New Building Block for Head-to-Head Polymer Semiconductors
journal, January 2013
- Guo, Xugang; Quinn, Jordan; Chen, Zhihua
- Journal of the American Chemical Society, Vol. 135, Issue 5
Head-to-Head Linkage Containing Bithiophene-Based Polymeric Semiconductors for Highly Efficient Polymer Solar Cells
journal, September 2016
- Shi, Shengbin; Liao, Qiaogan; Tang, Yumin
- Advanced Materials, Vol. 28, Issue 45
A Planar Copolymer for High Efficiency Polymer Solar Cells
journal, October 2009
- Qin, Ruiping; Li, Weiwei; Li, Cuihong
- Journal of the American Chemical Society, Vol. 131, Issue 41
Universal Correlation between Fibril Width and Quantum Efficiency in Diketopyrrolopyrrole-Based Polymer Solar Cells
journal, December 2013
- Li, Weiwei; Hendriks, Koen H.; Furlan, Alice
- Journal of the American Chemical Society, Vol. 135, Issue 50
Quenching to the Percolation Threshold in Organic Solar Cells
journal, February 2019
- Ye, Long; Li, Sunsun; Liu, Xiaoyu
- Joule, Vol. 3, Issue 2
Controlling Molecular Weight to Achieve High-Efficient Polymer Solar Cells With Unprecedented Fill Factor of 79% Based on Non-Fullerene Small Molecule Acceptor
journal, June 2018
- Xiong, Wentao; Qi, Feng; Liu, Tao
- Solar RRL, Vol. 2, Issue 9
Soft x-ray scattering facility at the Advanced Light Source with real-time data processing and analysis
journal, April 2012
- Gann, E.; Young, A. T.; Collins, B. A.
- Review of Scientific Instruments, Vol. 83, Issue 4
Blade-Cast Nonfullerene Organic Solar Cells in Air with Excellent Morphology, Efficiency, and Stability
journal, April 2018
- Zhang, Lin; Lin, Baojun; Hu, Bo
- Advanced Materials, Vol. 30, Issue 22
Enhancing the Performance of Organic Solar Cells by Hierarchically Supramolecular Self-Assembly of Fused-Ring Electron Acceptors
journal, June 2018
- Liu, Yahui; Zhang, Cai’e; Hao, Dan
- Chemistry of Materials, Vol. 30, Issue 13
Efficient inverted polymer solar cells employing favourable molecular orientation
journal, May 2015
- Vohra, Varun; Kawashima, Kazuaki; Kakara, Takeshi
- Nature Photonics, Vol. 9, Issue 6
Efficient Quaternary Organic Solar Cells with Parallel-Alloy Morphology
journal, January 2019
- Bi, Zhaozhao; Zhu, Qinglian; Xu, Xianbin
- Advanced Functional Materials, Vol. 29, Issue 9
Highly efficient and thermally stable fullerene-free organic solar cells based on a small molecule donor and acceptor
journal, January 2016
- Badgujar, Sachin; Song, Chang Eun; Oh, Sora
- Journal of Materials Chemistry A, Vol. 4, Issue 42
9.73% Efficiency Nonfullerene All Organic Small Molecule Solar Cells with Absorption-Complementary Donor and Acceptor
journal, March 2017
- Bin, Haijun; Yang, Yankang; Zhang, Zhi-Guo
- Journal of the American Chemical Society, Vol. 139, Issue 14
Ternary solar cells with a mixed face-on and edge-on orientation enable an unprecedented efficiency of 12.1%
journal, January 2017
- Kumari, Tanya; Lee, Sang Myeon; Kang, So-Huei
- Energy & Environmental Science, Vol. 10, Issue 1
Morphology and Phase Segregation of Spin-Casted Films of Polyfluorene/PCBM Blends
journal, November 2007
- Nilsson, Svante; Bernasik, Andrzej; Budkowski, Andrzej
- Macromolecules, Vol. 40, Issue 23
Modeling photocurrent action spectra of photovoltaic devices based on organic thin films
journal, July 1999
- Pettersson, Leif A. A.; Roman, Lucimara S.; Inganäs, Olle
- Journal of Applied Physics, Vol. 86, Issue 1, p. 487-496
Quantification of Quantum Efficiency and Energy Losses in Low Bandgap Polymer:Fullerene Solar Cells with High Open-Circuit Voltage
journal, May 2012
- Vandewal, Koen; Ma, Zaifei; Bergqvist, Jonas
- Advanced Functional Materials, Vol. 22, Issue 16
Fourier-transform photocurrent spectroscopy of microcrystalline silicon for solar cells
journal, February 2002
- Vanecek, M.; Poruba, A.
- Applied Physics Letters, Vol. 80, Issue 5
Radiative efficiency of state-of-the-art photovoltaic cells
journal, September 2011
- Green, Martin A.
- Progress in Photovoltaics: Research and Applications, Vol. 20, Issue 4, p. 472-476
Structure–property relationships of oligothiophene–isoindigo polymers for efficient bulk-heterojunction solar cells
journal, January 2014
- Ma, Zaifei; Sun, Wenjun; Himmelberger, Scott
- Energy Environ. Sci., Vol. 7, Issue 1
Origin of the Reduced Fill Factor and Photocurrent in MDMO-PPV:PCNEPV All-Polymer Solar Cells
journal, July 2007
- Mandoc, M. M.; Veurman, W.; Koster, L. J. A.
- Advanced Functional Materials, Vol. 17, Issue 13
Effect of Core Size on Performance of Fused-Ring Electron Acceptors
text, January 2018
- Z., Li,; W., You,; K., Liu,
- The University of North Carolina at Chapel Hill University Libraries
Naphthodithiophene-Based Nonfullerene Acceptor for High-Performance Organic Photovoltaics: Effect of Extended Conjugation
text, January 2018
- X., Zhan,; Y., Lin,; Y., Wu,
- The University of North Carolina at Chapel Hill University Libraries
Fused nonacyclic electron acceptors for efficient polymer solar cells
text, January 2017
- Qidan, Ling,; Qianqian, Zhang,; Wei, You,
- American Chemical Society
Quantification of Quantum Efficiency and Energy Losses in Low Bandgap Polymer:Fullerene Solar Cells with High Open-Circuit Voltage
journal, May 2012
- Vandewal, Koen; Ma, Zaifei; Bergqvist, Jonas
- Advanced Functional Materials, Vol. 22, Issue 16
An Electron Acceptor with Broad Visible-NIR Absorption and Unique Solid State Packing for As-Cast High Performance Binary Organic Solar Cells
journal, June 2018
- Shi, Xueliang; Liao, Xunfan; Gao, Ke
- Advanced Functional Materials, Vol. 28, Issue 33
Efficient Quaternary Organic Solar Cells with Parallel-Alloy Morphology
journal, January 2019
- Bi, Zhaozhao; Zhu, Qinglian; Xu, Xianbin
- Advanced Functional Materials, Vol. 29, Issue 9
Design and Synthesis of a Low Bandgap Small Molecule Acceptor for Efficient Polymer Solar Cells
journal, July 2016
- Yao, Huifeng; Chen, Yu; Qin, Yunpeng
- Advanced Materials, Vol. 28, Issue 37
Head-to-Head Linkage Containing Bithiophene-Based Polymeric Semiconductors for Highly Efficient Polymer Solar Cells
journal, September 2016
- Shi, Shengbin; Liao, Qiaogan; Tang, Yumin
- Advanced Materials, Vol. 28, Issue 45
Enhancing Performance of Nonfullerene Acceptors via Side-Chain Conjugation Strategy
journal, July 2017
- Wang, Jiayu; Wang, Wei; Wang, Xiaohui
- Advanced Materials, Vol. 29, Issue 35
Ternary Nonfullerene Polymer Solar Cells with 12.16% Efficiency by Introducing One Acceptor with Cascading Energy Level and Complementary Absorption
journal, November 2017
- Jiang, Weigang; Yu, Runnan; Liu, Zhiyang
- Advanced Materials, Vol. 30, Issue 1
Naphthodithiophene-Based Nonfullerene Acceptor for High-Performance Organic Photovoltaics: Effect of Extended Conjugation
journal, November 2017
- Zhu, Jingshuai; Ke, Zhifan; Zhang, Qianqian
- Advanced Materials, Vol. 30, Issue 2
An Unfused-Core-Based Nonfullerene Acceptor Enables High-Efficiency Organic Solar Cells with Excellent Morphological Stability at High Temperatures
journal, December 2017
- Li, Shuixing; Zhan, Lingling; Liu, Feng
- Advanced Materials, Vol. 30, Issue 6
Blade-Cast Nonfullerene Organic Solar Cells in Air with Excellent Morphology, Efficiency, and Stability
journal, April 2018
- Zhang, Lin; Lin, Baojun; Hu, Bo
- Advanced Materials, Vol. 30, Issue 22
Radiative efficiency of state-of-the-art photovoltaic cells
journal, September 2011
- Green, Martin A.
- Progress in Photovoltaics: Research and Applications, Vol. 20, Issue 4, p. 472-476
The effect of end-capping groups in A-D-A type non-fullerene acceptors on device performance of organic solar cells
journal, September 2017
- Jia, Jianchao; Zheng, Nannan; Wang, Zhenfeng
- Science China Chemistry, Vol. 60, Issue 11
A chlorinated low-bandgap small-molecule acceptor for organic solar cells with 14.1% efficiency and low energy loss
journal, July 2018
- Kan, Bin; Feng, Huanran; Yao, Huifeng
- Science China Chemistry, Vol. 61, Issue 10
Quenching to the Percolation Threshold in Organic Solar Cells
journal, February 2019
- Ye, Long; Li, Sunsun; Liu, Xiaoyu
- Joule, Vol. 3, Issue 2
Enhancing the Performance of Organic Solar Cells by Hierarchically Supramolecular Self-Assembly of Fused-Ring Electron Acceptors
journal, June 2018
- Liu, Yahui; Zhang, Cai’e; Hao, Dan
- Chemistry of Materials, Vol. 30, Issue 13
Universal Correlation between Fibril Width and Quantum Efficiency in Diketopyrrolopyrrole-Based Polymer Solar Cells
journal, December 2013
- Li, Weiwei; Hendriks, Koen H.; Furlan, Alice
- Journal of the American Chemical Society, Vol. 135, Issue 50
Phthalimide-Based Polymers for High Performance Organic Thin-Film Transistors
journal, June 2009
- Guo, Xugang; Kim, Felix Sunjoo; Jenekhe, Samson A.
- Journal of the American Chemical Society, Vol. 131, Issue 21, p. 7206-7207
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
Exploiting Noncovalently Conformational Locking as a Design Strategy for High Performance Fused-Ring Electron Acceptor Used in Polymer Solar Cells
journal, February 2017
- Liu, Yahui; Zhang, Zhe; Feng, Shiyu
- Journal of the American Chemical Society, Vol. 139, Issue 9
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
Morphology and Phase Segregation of Spin-Casted Films of Polyfluorene/PCBM Blends
journal, November 2007
- Nilsson, Svante; Bernasik, Andrzej; Budkowski, Andrzej
- Macromolecules, Vol. 40, Issue 23
Efficient inverted polymer solar cells employing favourable molecular orientation
journal, May 2015
- Vohra, Varun; Kawashima, Kazuaki; Kakara, Takeshi
- Nature Photonics, Vol. 9, Issue 6
Soft x-ray scattering facility at the Advanced Light Source with real-time data processing and analysis
journal, April 2012
- Gann, E.; Young, A. T.; Collins, B. A.
- Review of Scientific Instruments, Vol. 83, Issue 4
Fused nonacyclic electron acceptors for efficient polymer solar cells
text, January 2017
- Qidan, Ling,; Qianqian, Zhang,; Wei, You,
- American Chemical Society
Works referencing / citing this record:
Graphdiyne Derivative as Multifunctional Solid Additive in Binary Organic Solar Cells with 17.3% Efficiency and High Reproductivity
journal, February 2020
- Liu, Le; Kan, Yuanyuan; Gao, Ke
- Advanced Materials, Vol. 32, Issue 11
Evaporation‐Free Nonfullerene Flexible Organic Solar Cell Modules Manufactured by An All‐Solution Process
journal, September 2019
- Han, Yong Woon; Jeon, Sung Jae; Lee, Hyoung Seok
- Advanced Energy Materials, Vol. 9, Issue 42
Chalcogen‐Fused Perylene Diimides‐Based Nonfullerene Acceptors for High‐Performance Organic Solar Cells: Insight into the Effect of O, S, and Se
journal, December 2019
- Li, Gang; Wang, Shuaihua; Li, Dandan
- Solar RRL, Vol. 4, Issue 3
A monothiophene unit incorporating both fluoro and ester substitution enabling high-performance donor polymers for non-fullerene solar cells with 16.4% efficiency
journal, January 2019
- Sun, Huiliang; Liu, Tao; Yu, Jianwei
- Energy & Environmental Science, Vol. 12, Issue 11
High-efficiency ternary nonfullerene polymer solar cells with increased phase purity and reduced nonradiative energy loss
journal, January 2020
- Zhang, Cai'e; Jiang, Pengcheng; Zhou, Xiaobo
- Journal of Materials Chemistry A, Vol. 8, Issue 4
An A–D–D–A-type non-fullerene small-molecule acceptor with strong near-infrared absorption for high performance polymer solar cells
journal, January 2019
- Tan, Hua; Zheng, Xiangjun; Zhu, Jianing
- Journal of Materials Chemistry C, Vol. 7, Issue 42
Naphthalene core-based noncovalently fused-ring electron acceptors: effects of linkage positions on photovoltaic performances
journal, January 2019
- Zheng, Rui; Guo, Qingxin; Hao, Dan
- Journal of Materials Chemistry C, Vol. 7, Issue 48
Effect of Molecular Structures of Donor Monomers of Polymers on Photovoltaic Properties
journal, November 2019
- Qin, Ruiping; Guo, Deen; Ma, Heng
- ACS Omega, Vol. 4, Issue 21