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Utilizing Difluorinated Thiophene Units To Improve the Performance of Polymer Solar Cells

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Macromolecules 2019, 52, 17, 6523-6532
    Article

    Utilizing Difluorinated Thiophene Units To Improve the Performance of Polymer Solar Cells
    Click to copy article linkArticle link copied!

    • Jeromy J. Rech
      Jeromy J. Rech
      Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States
      More by Jeromy J. Rech
      Orcidhttp://orcid.org/0000-0001-7963-9357
    • Liang Yan
      Liang Yan
      Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States
      More by Liang Yan
      Orcidhttp://orcid.org/0000-0003-4122-7466
    • Zhengxing Peng
      Zhengxing Peng
      Department of Physics and Organic and Carbon Electronics Lab (ORaCEL), North Carolina State University, Raleigh, North Carolina 27695, United States
      More by Zhengxing Peng
    • Shuixing Dai
      Shuixing Dai
      Department of Materials Science and Engineering, College of Engineering, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Peking University, Beijing 100871, China
      More by Shuixing Dai
    • Xiaowei Zhan
      Xiaowei Zhan
      Department of Materials Science and Engineering, College of Engineering, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Peking University, Beijing 100871, China
      More by Xiaowei Zhan
      Orcidhttp://orcid.org/0000-0002-1006-3342
    • Harald Ade
      Harald Ade
      Department of Physics and Organic and Carbon Electronics Lab (ORaCEL), North Carolina State University, Raleigh, North Carolina 27695, United States
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    • Wei You*
      Wei You
      Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States
      *E-mail: [email protected]
      More by Wei You
      Orcidhttp://orcid.org/0000-0003-0354-1948
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    Macromolecules

    Cite this: Macromolecules 2019, 52, 17, 6523–6532
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.macromol.9b01168
    Published August 22, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    While there are numerous approaches to functionalize conjugated polymers for organic solar cells (OSCs), one widely adopted approach is fluorination. Of the many different locations for fluorination, one of the least studied is the conjugated linker which connects the donor and acceptor moieties; further, all existing reports primarily explore monofluorinated thiophene units. Herein, we synthesize and compare two conjugated polymers, HTAZ and dFT-HTAZ, which have different thiophene linkers. In HTAZ, a bare thiophene unit connects the donor and acceptor moieties, while dFT-HTAZ utilizes difluorinated thiophene (dFT) linkers. These polymers serve as the model system to explore the impact of dFT units in OSCs; additionally, this is the first publication to investigate polymers containing dFT units paired with non-fullerene acceptors. Compared to HTAZ, the incorporation of the dFT units maintained the optical properties while lowering the energy levels by ∼0.4 eV, which allowed for a much improved Voc value of ∼1 V. Importantly, when compared with the appropriate non-fullerene acceptor, dFT-HTAZ:ITIC-Th1 blends reached an efficiency of ∼10%, which is nearly 3× that of the nonfluorinated HTAZ. As most OSC polymers have thiophene linkers, using dFT units could serve as a proficient method to increase OSC performance in many polymer systems, especially those that do not have locations for functionalization on the acceptor moiety.

    Copyright © 2019 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.macromol.9b01168.

    • Synthetic details for monomers and polymer, 1H and 19F NMR spectra, characterization methods and device fabrication, DFT calculations, SCLC measurements, neat ITIC-Th1 GIWAXS, RSoXS profile, and line fitting for GIWAXS blends (PDF)

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    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 15 publications.

    1. Pingping Gong, Pengzhi Guo, Yufei Wang, Lihe Yan, Zezhou Liang, Mingqiang Ding, Junfeng Tong, Jianfeng Li, Yangjun Xia. Ultrafast Kinetics Investigation of a Fluorinated-Benzothiadiazole Polymer with an Increased Excited State Transition Dipole Moment Applied in Organic Solar Cells. ACS Applied Energy Materials 2021, 4 (9) , 9627-9638. https://doi.org/10.1021/acsaem.1c01763
    2. Jeromy James Rech, Liang Yan, Zhen Wang, Qianqian Zhang, Spencer Bradshaw, Harald Ade, Wei You. Functionalization of Benzotriazole-Based Conjugated Polymers for Solar Cells: Heteroatom vs Substituents. ACS Applied Polymer Materials 2021, 3 (1) , 30-41. https://doi.org/10.1021/acsapm.0c00761
    3. Adane Desta Fenta, Song-Fu Liao, Syuan-Wei Li, Chun-Fu Lu, Chin-Ti Chen. Increasing the Fluorine Substituent of Thieno[3,4-c]pyrrole-4,6-dione Terthiophene Copolymers Progressively Narrows the Nanofibrils and Enhances the Efficiency of Fullerene-Based Polymer Photovoltaics. Macromolecules 2020, 53 (16) , 7073-7083. https://doi.org/10.1021/acs.macromol.0c01042
    4. Pengjie Chao, Meigen Guo, Yulin Zhu, Hui Chen, Mingrui Pu, Hsin-Hsiang Huang, Hong Meng, Chuluo Yang, Feng He. Enhanced Photovoltaic Performance by Synergistic Effect of Chlorination and Selenophene π-Bridge. Macromolecules 2020, 53 (8) , 2893-2901. https://doi.org/10.1021/acs.macromol.0c00405
    5. Wenxia Cao, Fengying Dai, Rongrong Hu, Ben Zhong Tang. Economic Sulfur Conversion to Functional Polythioamides through Catalyst-Free Multicomponent Polymerizations of Sulfur, Acids, and Amines. Journal of the American Chemical Society 2020, 142 (2) , 978-986. https://doi.org/10.1021/jacs.9b11066
    6. Laura Crociani. The Double-Cross of Benzotriazole-Based Polymers as Donors and Acceptors in Non-Fullerene Organic Solar Cells. Molecules 2024, 29 (15) , 3625. https://doi.org/10.3390/molecules29153625
    7. Somayeh Kashani, Jeromy James Rech, Tuo Liu, Kyle Baustert, Abbas Ghaffari, Indunil Angunawela, Yuan Xiong, Abay Dinku, Wei You, Kenneth Graham, Harald Ade. Exciton Binding Energy in Organic Polymers: Experimental Considerations and Tuning Prospects. Advanced Energy Materials 2024, 14 (6) https://doi.org/10.1002/aenm.202302837
    8. Jie Zhang, Fan Ye, Jin-Lei Huo, Jian-Wen Peng, Rong-Rong Hu, Ben Zhong Tang. Diamines, CS2 and Monoisocyanide-participated Polymerizations for Large-scale Synthesis of Polythioureas and Thioformamide. Chinese Journal of Polymer Science 2023, 41 (10) , 1563-1576. https://doi.org/10.1007/s10118-023-3019-y
    9. Asif Mahmood, Ahmad Irfan, Jin-Liang Wang. Molecular level understanding of the chalcogen atom effect on chalcogen-based polymers through electrostatic potential, non-covalent interactions, excited state behaviour, and radial distribution function. Polymer Chemistry 2022, 13 (42) , 5993-6001. https://doi.org/10.1039/D2PY00960A
    10. Jeromy James Rech, Justin Neu, Yunpeng Qin, Stephanie Samson, Jordan Shanahan, Richard F. Josey, Harald Ade, Wei You. Designing Simple Conjugated Polymers for Scalable and Efficient Organic Solar Cells. ChemSusChem 2021, 14 (17) , 3561-3568. https://doi.org/10.1002/cssc.202100910
    11. Rong-Xian Jhang, Guan-Lin Chen, Rathinam Raja, Po-Tuan Chen, Michitoshi Hayashi, Syang-Peng Rwei, Shan-hui Hsu, Leeyih Wang. Difluoroterthiophene as promising block to build highly planar conjugated polymer for polymer photovoltaic cells. Dyes and Pigments 2021, 188 , 109206. https://doi.org/10.1016/j.dyepig.2021.109206
    12. Yang Bai, Ling-Wei Xue, Hai-Qiao Wang, Zhi-Guo Zhang. Research Advances on Benzotriazole-based Organic Photovoltaic Materials. Acta Chimica Sinica 2021, 79 (7) , 820. https://doi.org/10.6023/A21050193
    13. Gururaj P. Kini, Sung Jae Jeon, Doo Kyung Moon. Design Principles and Synergistic Effects of Chlorination on a Conjugated Backbone for Efficient Organic Photovoltaics: A Critical Review. Advanced Materials 2020, 32 (11) https://doi.org/10.1002/adma.201906175
    14. Lili An, Junfeng Tong, Yubo Huang, Zezhou Liang, Jianfeng Li, Chunyan Yang, Xunchang Wang. Elevated Photovoltaic Performance in Medium Bandgap Copolymers Composed of Indacenodi-thieno[3,2-b]thiophene and Benzothiadiazole Subunits by Modulating the π-Bridge. Polymers 2020, 12 (2) , 368. https://doi.org/10.3390/polym12020368
    15. Siyu Mao, Jordan H. Kramer, Haoran Sun. Redox-active fluoropolymers. 2020, 115-141. https://doi.org/10.1016/B978-0-12-821873-0.00004-7
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    Macromolecules

    Cite this: Macromolecules 2019, 52, 17, 6523–6532
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.macromol.9b01168
    Published August 22, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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