Covalently Bound Clusters of Alpha-Substituted PDI—Rival Electron Acceptors to Fullerene for Organic Solar Cells

Wu, Qinghe; Zhao, Donglin; Schneider, Alexander M.; Chen, Wei; Yu, Luping

doi:10.1021/jacs.6b03562

Title: Covalently Bound Clusters of Alpha-Substituted PDI—Rival Electron Acceptors to Fullerene for Organic Solar Cells

Journal Article · Tue May 24 00:00:00 EDT 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b03562· OSTI ID:1352625

Wu, Qinghe ^[1]; Zhao, Donglin ^[2]; Schneider, Alexander M. ^[2]; Chen, Wei ^[3]; Yu, Luping ^[2]

Univ. of Chicago, IL (United States). James Franck Inst., Dept. of Chemistry
Univ. of Chicago, IL (United States). James Franck Inst., Dept. of Chemistry
Argonne National Lab. (ANL), Argonne, IL (United States). Materials Science Division; Univ. of Chicago, IL (United States). Inst. for Molecular Engineering

Here, a cluster type of electron acceptor, TPB, bearing four α-perylenediimides (PDIs), was developed, in which the four PDIs form a cross-like molecular conformation while still partially conjugated with the BDT-Th core. The blend TPB:PTB7-Th films shows favorable morphology and efficient charge dissociation. The inverted solar cells exhibited the highest PCE of 8.47 % with the extraordinary high J_sc values (>18 mA/cm²), comparable with those of the corresponding PC₇₁BM/PBT7-Th based solar cells.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

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

Grant/Contract Number:: AC02-06CH11357; DMR-1263006; SC0001059

OSTI ID:: 1352625

Journal Information:: Journal of the American Chemical Society, Vol. 138, Issue 23; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 362 works

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Naphtho[2,3-b]thiophene diimide (NTI): a mono-functionalisable core-extended naphthalene diimide for electron-deficient architectures Chen, Wangqiao; Nakano, Masahiro; Kim, Ji-Hoon Journal of Materials Chemistry C, Vol. 4, Issue 38 https://doi.org/10.1039/c6tc03476d	journal	January 2016
Constructing a donor–acceptor linear-conjugation structure for heterologous perylene diimides to greatly improve the photovoltaic performance Wang, Helin; Chen, Lingcheng; Xiao, Yi Journal of Materials Chemistry C, Vol. 7, Issue 4 https://doi.org/10.1039/c8tc04929g	journal	January 2019
Effects of water vapor and oxygen on non-fullerene small molecule acceptors Wang, Chuanfei; Ni, Shaofei; Braun, Slawomir Journal of Materials Chemistry C, Vol. 7, Issue 4 https://doi.org/10.1039/c8tc05475d	journal	January 2019
Nonfullerene Acceptors for Semitransparent Organic Solar Cells Dai, Shuixing; Zhan, Xiaowei Advanced Energy Materials, Vol. 8, Issue 21 https://doi.org/10.1002/aenm.201800002	journal	May 2018
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Systematic evaluation of structure–property relationships in heteroacene – diketopyrrolopyrrole molecular donors for organic solar cells Loser, Stephen; Lou, Sylvia J.; Savoie, Brett M. Journal of Materials Chemistry A, Vol. 5, Issue 19 https://doi.org/10.1039/c7ta02037f	journal	January 2017
Non-fullerene acceptors for organic solar cells Yan, Cenqi; Barlow, Stephen; Wang, Zhaohui Nature Reviews Materials, Vol. 3, Issue 3 https://doi.org/10.1038/natrevmats.2018.3	journal	February 2018
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Design, synthesis, and structural characterization of the first dithienocyclopentacarbazole-based n-type organic semiconductor and its application in non-fullerene polymer solar cells Cao, Qunfang; Xiong, Wentao; Chen, Huajie Journal of Materials Chemistry A, Vol. 5, Issue 16 https://doi.org/10.1039/c7ta01143a	journal	January 2017
Electronic and optical properties of π-bridged perylenediimide derivatives: the role of π-bridges Guo, Yuan; Han, Guangchao; Tu, Zeyi Journal of Materials Chemistry A, Vol. 7, Issue 20 https://doi.org/10.1039/c9ta03124c	journal	January 2019
Isomerization of Perylene Diimide Based Acceptors Enabling High‐Performance Nonfullerene Organic Solar Cells with Excellent Fill Factor Luo, Zhenghui; Liu, Tao; Chen, Zhanxiang Advanced Science, Vol. 6, Issue 6 https://doi.org/10.1002/advs.201802065	journal	January 2019
Progress in the synthesis of perylene bisimide dyes Nowak-Król, Agnieszka; Würthner, Frank Organic Chemistry Frontiers, Vol. 6, Issue 8 https://doi.org/10.1039/c8qo01368c	journal	January 2019
Pyran-annulated perylene diimide derivatives as non-fullerene acceptors for high performance organic solar cells Li, Gang; Zhang, Yu; Liu, Tao Journal of Materials Chemistry C, Vol. 6, Issue 41 https://doi.org/10.1039/c8tc02823k	journal	January 2018
Rylene annulated phthalocyanine: a fully conjugated block for the construction of a supramolecular two-dimensional framework Feng, Jiajing; Fu, Lulu; Huang, Tengda Chemical Communications, Vol. 54, Issue 53 https://doi.org/10.1039/c8cc01216d	journal	January 2018
Novel dithiano-thieno fused perylene diimides: synthesis, characterization and application in organic thin-film transistors (OTFTs) Li, Gang; Li, Dandan; Liu, Xitong Chemical Communications, Vol. 55, Issue 65 https://doi.org/10.1039/c9cc04133h	journal	January 2019
Material insights and challenges for non-fullerene organic solar cells based on small molecular acceptors Zhang, Jianquan; Tan, Huei Shuan; Guo, Xugang Nature Energy, Vol. 3, Issue 9 https://doi.org/10.1038/s41560-018-0181-5	journal	July 2018
A universal nonfullerene electron acceptor matching with different band-gap polymer donors for high-performance polymer solar cells Luo, Zhenghui; Li, Guanghao; Gao, Wei Journal of Materials Chemistry A, Vol. 6, Issue 16 https://doi.org/10.1039/c7ta11339k	journal	January 2018
A three-dimensional thiophene-annulated perylene bisimide as a fullerene-free acceptor for a high performance polymer solar cell with the highest PCE of 8.28% and a V _OC over 1.0 V Luo, Zhenghui; Liu, Tao; Cheng, Wanli Journal of Materials Chemistry C, Vol. 6, Issue 5 https://doi.org/10.1039/c7tc05261h	journal	January 2018
A new nonfullerene acceptor based on perylene diimides for organic solar cells Liu, Zhitian; Wu, Yao; Jiang, Huanxiang Journal of Materials Science: Materials in Electronics, Vol. 29, Issue 12 https://doi.org/10.1007/s10854-018-9094-0	journal	April 2018
Ternary Polymer Solar Cells with High Efficiency of 14.24% by Integrating Two Well‐Complementary Nonfullerene Acceptors Jiang, Huanxiang; Li, Xiaoming; Wang, Jianing Advanced Functional Materials, Vol. 29, Issue 34 https://doi.org/10.1002/adfm.201903596	journal	June 2019
Dithieno[3,2- b :2′,3′- d ]pyrrol Fused Nonfullerene Acceptors Enabling Over 13% Efficiency for Organic Solar Cells Sun, Jia; Ma, Xiaoling; Zhang, Zhuohan Advanced Materials, Vol. 30, Issue 16 https://doi.org/10.1002/adma.201707150	journal	March 2018
Enhancing the Performance of Polymer Solar Cells via Core Engineering of NIR-Absorbing Electron Acceptors Dai, Shuixing; Li, Tengfei; Wang, Wei Advanced Materials, Vol. 30, Issue 15 https://doi.org/10.1002/adma.201706571	journal	March 2018
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High‐Performance Fluorinated Fused‐Ring Electron Acceptor with 3D Stacking and Exciton/Charge Transport Dai, Shuixing; Zhou, Jiadong; Chandrabose, Sreelakshmi Advanced Materials, Vol. 32, Issue 21 https://doi.org/10.1002/adma.202000645	journal	April 2020
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Achieving a High Fill Factor and Stability in Perylene Diimide–Based Polymer Solar Cells Using the Molecular Lock Effect between 4,4′‐Bipyridine and a Tri(8‐hydroxyquinoline)aluminum(III) Core Zhang, Guangjun; Xu, Xiaopeng; Lee, Young Woong Advanced Functional Materials, Vol. 29, Issue 29 https://doi.org/10.1002/adfm.201902079	journal	May 2019
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Fused Hexacyclic Nonfullerene Acceptor with Strong Near-Infrared Absorption for Semitransparent Organic Solar Cells with 9.77% Efficiency Wang, Wei; Yan, Cenqi; Lau, Tsz-Ki Advanced Materials, Vol. 29, Issue 31 https://doi.org/10.1002/adma.201701308	journal	June 2017
Side-Chain Impact on Molecular Orientation of Organic Semiconductor Acceptors: High Performance Nonfullerene Polymer Solar Cells with Thick Active Layer over 400 nm Luo, Zhenghui; Sun, Chenkai; Chen, Shanshan Advanced Energy Materials, Vol. 8, Issue 23 https://doi.org/10.1002/aenm.201800856	journal	June 2018
Side-Chain Optimization of Phthalimide−Bithiophene Copolymers for Efficient All-Polymer Solar Cells with Large Fill Factors Chen, Jianhua; Qiu, Fanglong; Liao, Qiaogan Asian Journal of Organic Chemistry, Vol. 7, Issue 11 https://doi.org/10.1002/ajoc.201800156	journal	May 2018
Electron Delocalization in Perylene Diimide Helicenes Schuster, Nathaniel J.; Paley, Daniel W.; Jockusch, Steffen Angewandte Chemie, Vol. 128, Issue 43 https://doi.org/10.1002/ange.201607878	journal	September 2016
Isomeric N-Annulated Perylene Diimide Dimers for Organic Solar Cells Ma, Zetong; Fu, Huiting; Meng, Dong Chemistry - An Asian Journal, Vol. 13, Issue 8 https://doi.org/10.1002/asia.201800058	journal	March 2018
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Development of n-Type Porphyrin Acceptors for Panchromatic Light-Harvesting Fullerene-Free Organic Solar Cells Lee, Un-Hak; Hadmojo, Wisnu Tantyo; Kim, Junho Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00473	journal	October 2018
Fine-Tuning of Molecular Packing and Energy Level through Methyl Substitution Enabling Excellent Small Molecule Acceptors for Nonfullerene Polymer Solar Cells with Efficiency up to 12.54% Luo, Zhenghui; Bin, Haijun; Liu, Tao Advanced Materials, Vol. 30, Issue 9 https://doi.org/10.1002/adma.201706124	journal	January 2018
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Single-Junction Binary-Blend Nonfullerene Polymer Solar Cells with 12.1% Efficiency Fuwen, Zhao,; Li, Jiang,; Shuixing, Dai, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/2de3-a253	text	January 2017
High-Efficiency Nonfullerene Organic Solar Cells: Critical Factors that Affect Complex Multi-Length Scale Morphology and Device Performance Ye, Long; Zhao, Wenchao; Li, Sunsun Advanced Energy Materials, Vol. 7, Issue 7 https://doi.org/10.1002/aenm.201602000	journal	December 2016
Star‐Shaped and Fused Electron Acceptors based on C _{3 h} ‐Symmetric Coplanar Trindeno[1, 2‐b: 4, 5‐b′: 7, 8‐b′′]trithiophene Core for Non‐Fullerene Solar Cells Wang, Weijie; Wu, Xiaofu; Hang, Hao Chemistry – A European Journal https://doi.org/10.1002/chem.201804554	journal	December 2018
Effects of conjugated bridges on the photovoltaic properties of ortho -functionalized perylene diimides for non-fullerene polymer solar cells Wu, Jiazun; Li, Xiangchun; Liu, Xiaodong Journal of Materials Chemistry C, Vol. 6, Issue 48 https://doi.org/10.1039/c8tc03303j	journal	January 2018
Electron-Transporting Bis(heterotetracenes) with Tunable Helical Packing Zeng, Cheng; Xiao, Chengyi; Feng, Xinliang Angewandte Chemie International Edition, Vol. 57, Issue 34 https://doi.org/10.1002/anie.201805614	journal	June 2018
Fine-Tuning the Energy Levels of a Nonfullerene Small-Molecule Acceptor to Achieve a High Short-Circuit Current and a Power Conversion Efficiency over 12% in Organic Solar Cells. Kan, Bin; Zhang, Jiangbin; Liu, Feng Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.20603	text	January 2018
A Novel Thiophene-fused Ending Group Enabling an Excellent Small Molecule Acceptor for High-performance Fullerene-free Polymer Solar Cells with 11.8% Efficiency Xie, Dongjun; Liu, Tao; Gao, Wei arXiv https://doi.org/10.48550/arxiv.1703.02896	preprint	January 2017
The Role of the Axial Substituent in Subphthalocyanine Acceptors for Bulk-Heterojunction Solar Cells Duan, Chunhui; Zango, Germán; García Iglesias, Miguel Angewandte Chemie International Edition, Vol. 56, Issue 1 https://doi.org/10.1002/anie.201608644	journal	November 2016
Morphological Evolution of Tetrachlorinated Perylene Bisimides with Lengthy Alkyl Substituent Polycrystalline Thin Films during Reversible Phase Transitions Xin, Rui; Wang, Shaojuan; Zeng, Cheng ACS Omega, Vol. 5, Issue 1 https://doi.org/10.1021/acsomega.9b03675	journal	December 2019
Utilizing Benzotriazole and Indacenodithiophene Units to Construct Both Polymeric Donor and Small Molecular Acceptors to Realize Organic Solar Cells With High Open-Circuit Voltages Beyond 1.2 V Tang, Ailing; Chen, Fan; Xiao, Bo Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00147	journal	May 2018
Small-Molecule Electron Acceptors for Efficient Non-fullerene Organic Solar Cells Zhang, Zhenzhen; Yuan, Jun; Wei, Qingya Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00414	journal	September 2018

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