a.Department of Chemistry, School of Science, Beijing Jiaotong University, Beijing 100044, China
b.Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China
c.College of Basic Medicine, Hebei University, Baoding 071002, China
yhxu@bjtu.edu.cn (Y.H.X.)
chenqm@mail.buct.edu.cn (Q.M.C.)
liweiwei@iccas.ac.cn (W.W.L.)
收稿:2022-01-13,
修回:2022-2-21,
录用:2022-3-7,
网络首发:2022-05-27,
纸质出版:2022-08-01
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Liu, B. Q.; Xu, Y. H.; Liu, F.; Xie, C. C.; Liang, S. J.; Chen, Q. M.; Li, W. W. Double-cable conjugated polymers with fullerene pendant for single-component organic solar cells. Chinese J. Polym. Sci. 2022, 40, 898–904
Bai-Qiao Liu, Yun-Hua Xu, Feng Liu, et al. Double-Cable Conjugated Polymers with Fullerene Pendant for Single-Component Organic Solar Cells[J]. Chinese Journal of Polymer Science, 2022, 40(8): 898-904.
Liu, B. Q.; Xu, Y. H.; Liu, F.; Xie, C. C.; Liang, S. J.; Chen, Q. M.; Li, W. W. Double-cable conjugated polymers with fullerene pendant for single-component organic solar cells. Chinese J. Polym. Sci. 2022, 40, 898–904 DOI: 10.1007/s10118-022-2732-2.
Bai-Qiao Liu, Yun-Hua Xu, Feng Liu, et al. Double-Cable Conjugated Polymers with Fullerene Pendant for Single-Component Organic Solar Cells[J]. Chinese Journal of Polymer Science, 2022, 40(8): 898-904. DOI: 10.1007/s10118-022-2732-2.
Double-cable conjugated polymers with fullerene pendant were synthesized via “functionalization-polymerization” method. The power conversion efficiencies (PCEs) based on these polymers increased from 0.71% to 1.71% with the enhanced fullerene contents.
In this work
the “functionalization-polymerization” (FP) method has been used to construct fullerene-contained double-cable conjugated polymers with “donor-acceptor” backbones. It was realized
via
synthesizing a fullerene-contained monomer and performing Stille polymerization. With this method
a series of double-cable conjugated polymers with different fullerene contents were developed and applied into single-component organic solar cells. The power conversion efficiencies (PCEs) based on these polymers increased from 0.71% to 1.71% with the enhanced fullerene contents. The relatively low PCEs might be originated from the poor microstructure in these polymers. These new conjugated polymers with molecular heterojunction would show potential application in organic electronic devices.
Ma, W.; Yang, C.; Gong, X.; Lee, K.; Heeger, A. J . Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology . Adv. Funct. Mater. , 2005 . 15 1617 - 1622 . DOI: 10.1002/adfm.200500211 http://doi.org/10.1002/adfm.200500211 .
Cheng, Y. J.; Yang, S. H.; Hsu, C. S . Synthesis of conjugated polymers for organic solar cell applications . Chem. Rev. , 2009 . 109 5868 - 5923 . DOI: 10.1021/cr900182s http://doi.org/10.1021/cr900182s .
Dou, L.; Liu, Y.; Hong, Z.; Li, G.; Yang, Y . Low-bandgap near-IR conjugated polymers/molecules for organic electronics . Chem. Rev. , 2015 . 115 12633 - 12665 . DOI: 10.1021/acs.chemrev.5b00165 http://doi.org/10.1021/acs.chemrev.5b00165 .
Yang, H.; Wu, Y.; Dong, Y.; Cui, C.; Li, Y . Random polymer donor for high-performance polymer solar cells with efficiency over 14% . ACS Appl. Mater. Interfaces , 2019 . 11 40339 - 40346 . DOI: 10.1021/acsami.9b14133 http://doi.org/10.1021/acsami.9b14133 .
Howard, J. B.; Thompson, B. C . Design of random and semi-random conjugated polymers for organic solar cells . Macromol. Chem. Phys. , 2017 . 218 1700255 DOI: 10.1002/macp.201700255 http://doi.org/10.1002/macp.201700255 .
Wu, M.; Shi, L.; Hu, Y.; Chen, L.; Hu, T.; Zhang, Y.; Yuan, Z.; Chen, Y . Additive-free non-fullerene organic solar cells with random copolymers as donors over 9% power conversion efficiency . Chin. Chem. Lett. , 2019 . 30 1161 - 1167 . DOI: 10.1016/j.cclet.2019.04.029 http://doi.org/10.1016/j.cclet.2019.04.029 .
Wu, Y.; Guo, J.; Wang, W.; Chen, Z.; Chen, Z.; Sun, R.; Wu, Q.; Wang, T.; Hao, X.; Zhu, H.; Min, J . A conjugated donor-acceptor block copolymer enables over 11% efficiency for single-component polymer solar cells . Joule , 2021 . 5 1800 - 1815 . DOI: 10.1016/j.joule.2021.05.002 http://doi.org/10.1016/j.joule.2021.05.002 .
Xu, W.; Zhang, M.; Xiao, J.; Zeng, M.; Ye, L.; Weng, C.; Zhao, B.; Zhang, J.; Tan, S . Improved photovoltaic properties of pm6-based terpolymer donors containing benzothiadiazole with a siloxane-terminated side chain . Polym. Chem. , 2020 . 11 6178 - 6186 . .
Lee, Y.; Gomez, E. D . Challenges and opportunities in the development of conjugated block copolymers for photovoltaics . Macromolecules , 2015 . 48 7385 - 7395 . DOI: 10.1021/acs.macromol.5b00112 http://doi.org/10.1021/acs.macromol.5b00112 .
Schraff, S.; Maity, S.; Schleeper, L.; Dong, Y.; Lucas, S.; Bakulin, A. A.; von Hauff, E.; Pammer, F . All-conjugated donor-acceptor block copolymers featuring a pentafulvenyl-polyisocyanide-acceptor . Polym. Chem. , 2020 . 11 1852 - 1859 . DOI: 10.1039/C9PY01879D http://doi.org/10.1039/C9PY01879D .
Bendejacq, D.; Ponsinet, V.; Joanicot, M.; Airiau, M . Chemical tuning of the microphase separation in diblock copolymers from controlled radical polymerization . Macromolecules , 2003 . 36 7289 - 7295 . DOI: 10.1021/ma0302661 http://doi.org/10.1021/ma0302661 .
Yang, C.; Lee, J. K.; Heeger, A. J.; Wudl, F . Well-defined donor-acceptor rod-coil diblock copolymers based on P3HT containing C60: the morphology and role as a surfactant in bulk-heterojunction solar cells . J. Mater. Chem. , 2009 . 19 5416 - 5423 . DOI: 10.1039/b901732a http://doi.org/10.1039/b901732a .
Wang, J.; Higashihara, T . Synthesis of all-conjugated donor-acceptor block copolymers and their application in all-polymer solar cells . Polym. Chem. , 2013 . 4 5518 - 5526 . DOI: 10.1039/c3py00979c http://doi.org/10.1039/c3py00979c .
Rahmanudin, A.; Yao, L.; Sekar, A.; Cho, H. H.; Liu, Y.; Lhermitte, C. R.; Sivula, K . Fully conjugated donor-acceptor block copolymers for organic photovoltaics via Heck-Mizoroki coupling . ACS Macro Lett. , 2019 . 8 134 - 139 . DOI: 10.1021/acsmacrolett.8b00932 http://doi.org/10.1021/acsmacrolett.8b00932 .
Park, C. G.; Park, S. H.; Kim, Y.; Nguyen, T. L.; Woo, H. Y.; Kang, H.; Yoon, H. J.; Park, S.; Cho, M. J.; Choi, D. H . Facile one-pot polymerization of a fully conjugated donor–acceptor block copolymer and its application in efficient single component polymer solar cells . J. Mater. Chem. A , 2019 . 7 21280 - 21289 . DOI: 10.1039/C9TA06107J http://doi.org/10.1039/C9TA06107J .
Park, S. H.; Kim, Y.; Kwon, N. Y.; Lee, Y. W.; Woo, Han, Y.; Chae, W. S.; Park, S.; Cho; M. J.; Choi, D. H . Significantly improved morphology and efficiency of nonhalogenated solvent-processed solar cells derived from a conjugated donor–acceptor block copolymer . Adv. Sci. , 2020 . 7 1902470 DOI: 10.1002/advs.201902470 http://doi.org/10.1002/advs.201902470 .
Roncali, J.; Grosu, I . The dawn of single material organic solar cells . Adv. Sci. , 2019 . 6 1801026 DOI: 10.1002/advs.201801026 http://doi.org/10.1002/advs.201801026 .
Liang, S.; Jiang, X.; Xiao, C.; Li, C.; Li, W . Double-cable conjugated polymers with pendant rylene diimides for single-component organic solar cells . Acc. Chem. Res. , 2021 . 54 2227 - 2237 . DOI: 10.1021/acs.accounts.1c00070 http://doi.org/10.1021/acs.accounts.1c00070 .
Yamamoto, S.; Yasuda, H.; Ohkita, H.; Benten, H.; Ito, S.; Miyanishi, S.; Tajima, K.; Hashimoto, K . Charge generation and recombination in fullerene-attached poly(3-hexylthiophene)-based diblock copolymer films . J. Phys. Chem. C , 2014 . 118 10584 - 10589 . DOI: 10.1021/jp4126683 http://doi.org/10.1021/jp4126683 .
Pierini, F.; Lanzi, M.; Nakielski, P.; Pawłowska, S.; Urbanek, O.; Zembrzycki, K.; Kowalewski, T. A . Single-material organic solar cells based on electrospun fullerene-grafted polythiophene nanofibers . Macromolecules , 2017 . 50 4972 - 4981 . DOI: 10.1021/acs.macromol.7b00857 http://doi.org/10.1021/acs.macromol.7b00857 .
Iftikhar, S.; Aslam, S.; Butt, N. Z.; Ashraf, R. S.; Yameen, B . Prato reaction derived polythiophene/C60 donor-acceptor double cable polymer, fabrication of photodetectors and evaluation of photocurrent generation . J. Mater. Chem. C , 2020 . 8 17365 - 17373 . DOI: 10.1039/D0TC03344H http://doi.org/10.1039/D0TC03344H .
Chen, P.; Nakano, K.; Suzuki, K.; Hashizume, D.; Koganezawa, T.; Tajima, K . Organic solar cells with controlled nanostructures based on microphase separation of fullerene-attached thiophene-selenophene heteroblock copolymers . ACS Appl. Mater. Interfaces , 2017 . 9 4758 - 4768 . DOI: 10.1021/acsami.6b14629 http://doi.org/10.1021/acsami.6b14629 .
Miyanishi, S.; Zhang, Y.; Hashimoto, K.; Tajima, K . Controlled synthesis of fullerene-attached poly(3-alkylthiophene)-based copolymers for rational morphological design in polymer photovoltaic devices . Macromolecules , 2012 . 45 6424 - 6437 . DOI: 10.1021/ma300376m http://doi.org/10.1021/ma300376m .
Miyanishi, S.; Zhang, Y.; Tajima, K.; Hashimoto, K . Fullerene attached all-semiconducting diblock copolymers for stable single-component polymer solar cells . Chem. Commun. , 2010 . 46 6723 - 6725 . DOI: 10.1039/c0cc01819h http://doi.org/10.1039/c0cc01819h .
Tan, Z.; Hou, J.; He, Y.; Zhou, E.; Li, Y . Synthesis and photovoltaic properties of a donor−acceptor double-cable polythiophene with high content of C60 pendant . Macromolecules , 2007 . 40 1868 - 1873 . DOI: 10.1021/ma070052+ http://doi.org/10.1021/ma070052+ .
He, Y.; Li, N.; Brabec, C. J . Single-component organic solar cells with competitive performance . Org. Mater. , 2021 . 03 228 - 244 . DOI: 10.1055/s-0041-1727234 http://doi.org/10.1055/s-0041-1727234 .
Roncali, J . Single material solar cells: The next frontier for organic photovoltaics? . Adv. Energy Mater. , 2011 . 1 147 - 160 . DOI: 10.1002/aenm.201000008 http://doi.org/10.1002/aenm.201000008 .
Yu, P.; Feng, G.; Li, J.; Li, C.; Xu, Y.; Xiao, C.; Li, W . A selenophene substituted double-cable conjugated polymer enables efficient single-component organic solar cells . J. Mater. Chem. C , 2020 . 8 2790 - 2797 . DOI: 10.1039/C9TC06667E http://doi.org/10.1039/C9TC06667E .
Jiang, X. D.; Yang, J. J.; Karuthedath, S; Li, J.; Lai, W.; Li, C.; Xiao, C.; Ye, L.; Mai, Z.; Tang, Z.; Laquai, F.; Li, W . Miscibility-controlled phase separation in double-cable conjugated polymers for single-component organic solar cells with efficiencies over 8% . Angew. Chem. Int. Ed. , 2020 . 59 21683 - 21692 . DOI: 10.1002/anie.202009272 http://doi.org/10.1002/anie.202009272 .
Yang, F.; Li, J.; Li, C.; Li, W . Improving electron transport in a double-cable conjugated polymer via parallel perylenetriimide design . Macromolecules , 2019 . 52 3689 - 3696 . DOI: 10.1021/acs.macromol.9b00495 http://doi.org/10.1021/acs.macromol.9b00495 .
Liang, S.; Xu, Y.; Li, C.; Li, J.; Wang, D.; Li, W . Realizing lamellar nanophase separation in a double-cable conjugated polymer via a solvent annealing process . Polym. Chem. , 2019 . 10 4584 - 4592 . DOI: 10.1039/C9PY00765B http://doi.org/10.1039/C9PY00765B .
Feng, G.; Li, J.; He, Y.; Zheng, W.; Wang, J.; Li, C.; Tang, Z.; Osvet, A.; Li, N.; Brabec, C. J.; Li, Y.; Yan, H.; Li, W . Thermal-driven phase separation of double-cable polymers enables efficient single-component organic solar cells . Joule , 2019 . 3 1765 - 1781 . DOI: 10.1016/j.joule.2019.05.008 http://doi.org/10.1016/j.joule.2019.05.008 .
Yang, F.; Wang, X.; Feng, G.; Ma, J.; Li, C.; Li, J.; Ma, W.; Li, W . A new strategy for designing polymer electron acceptors: electronrich conjugated backbone with electron-deficient side units . Sci. China Chem. , 2018 . 61 824 - 829 . DOI: 10.1007/s11426-018-9241-0 http://doi.org/10.1007/s11426-018-9241-0 .
Lai, W.; Li, C.; Zhang, J., Yang, F.; Colberts, F. J. M.; Guo, B.; Wang, Q. M.; Li, M.; Zhang, A.; Janssen, R. A. J.; Zhang, M.; Li, W . Diketopyrrolopyrrole-based conjugated polymers with perylene bisimide side chains for single-component organic solar cells . Chem. Mater. , 2017 . 29 7073 - 7077 . DOI: 10.1021/acs.chemmater.7b02534 http://doi.org/10.1021/acs.chemmater.7b02534 .
Feng, G.; Li, J.; Colberts, F. J. M.; Li, M.; Zhang, J.; Yang, F.; Jin, Y.; Zhang, F.; Janssen, R. A. J.; Li, C.; Li, W . “Double-cable” conjugated polymers with linear backbone toward high quantum efficiencies in single-component polymer solar cells . J. Am. Chem. Soc. , 2017 . 139 18647 - 18656 . DOI: 10.1021/jacs.7b10499 http://doi.org/10.1021/jacs.7b10499 .
Li, S.; Yuan, X.; Zhang, Q.; Li, B.; Li, Y.; Sun, J.; Feng, Y.; Zhang, X.; Wu, Z.; Wei, H.; Wang, M.; Hu, Y.; Zhang, Y.; Woo, H. Y.; Yuan, J.; Ma, W . Narrow-bandgap single-component polymer solar cells with approaching 9% efficiency . Adv. Mater. , 2021 . 33 2101295 DOI: 10.1002/adma.202101295 http://doi.org/10.1002/adma.202101295 .
Liu, Y.; Liu, B.; Ma, C. Q.; Huang, F.; Bo, Z . Recent progress in organic solar cells (part i material science) . Sci. China Chem. , 2022 . 65 224 - 268 . DOI: 10.1007/s11426-021-1180-6 http://doi.org/10.1007/s11426-021-1180-6 .
He, Y.; Heumüller, T.; Lai, W.; Feng, G.; Classen, A.; Du, X.; Liu, C.; Li, W.; Li, N.; Brabec, C. J . Evidencing excellent thermal- and photostability for single-component organic solar cells with inherently built-in microstructure . Adv. Energy Mater. , 2019 . 9 1900409 DOI: 10.1002/aenm.201900409 http://doi.org/10.1002/aenm.201900409 .
Xie, C. C.; Jiang, X. D.; Zhu, Q. L.; Wang, D.; Xiao, C.; Liu, C.; Ma, W.; Chen, Q.; Li, W . Mechanical robust flexible single-component organic solar cells . Small Methods , 2021 . 5 2100481 DOI: 10.1002/smtd.202100481 http://doi.org/10.1002/smtd.202100481 .
Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Sozzani, P.; Zotti, G . The first “charm bracelet” conjugated polymer: an electroconducting polythiophene with covalently bound fullerene moieties . Angew. Chem. Int. Ed. , 1996 . 35 648 - 651 . DOI: 10.1002/anie.199606481 http://doi.org/10.1002/anie.199606481 .
Jousselme, B.; Blanchard, P.; Levillain, E.; de Bettignies, R.; Roncali, J . Electrochemical synthesis of C60-derivatized poly(thiophene)s from tailored precursors . Macromolecules , 2003 . 36 3020 - 3025 . DOI: 10.1021/ma034047r http://doi.org/10.1021/ma034047r .
Cravino, A.; Zerza, G.; Maggini, M.; Bucella, S.; Svensson, M; Andersson, M. R.; Neugebauer, H.; Sariciftci, N. S . A novel polythiophene with pendant fullerenes: toward donor/acceptor double-cable polymers . Chem. Commun. , 2000 . 2487 - 2488 . .
Cravino, A.; Zerza, G.; Neugebauer, H.; Maggini, M.; Sariciftci, N. S . Electrochemical and photophysical properties of a novel polythiophene with pendant fulleropyrrolidine moieties: toward “double cable” polymers for optoelectronic devices . J. Phys. Chem. B , 2002 . 106 70 - 76 . DOI: 10.1021/jp013077y http://doi.org/10.1021/jp013077y .
Ramos, A. M.; Rispens, M. T.; van Duren, J. K.; Hummelen, J. C.; Jassen, R. A. J . Photoinduced electron transfer and photovoltaic devices of a conjugated polymer with pendant fullerenes . J. Am. Chem. Soc. , 2001 . 123 6714 - 6715 . DOI: 10.1021/ja015614y http://doi.org/10.1021/ja015614y .
Zhang, F. L.; Svensson, M.; Andersson, M. R.; Maggini, M.; Inganäs, O . Soluble polythiophenes with pendant fullerene groups as double cable materials for photodiodes . Adv. Mater. , 2001 . 13 1871 - 1871 . DOI: 10.1002/1521-4095(200112)13:24<1871::AID-ADMA1871>3.0.CO;2-3 http://doi.org/10.1002/1521-4095(200112)13:24<1871::AID-ADMA1871>3.0.CO;2-3 .
Jia, J.; Huang, Q.; Jia, T.; Zhang, K.; Zhang, J.; Miao, J.; Huang, F.; Yang, C . Fine-tuning batch factors of polymer acceptors enables a binary all-polymer solar cell with high efficiency of 16.11% . Adv. Energy Mater. , 2022 . 12 2103193 DOI: 10.1002/aenm.202103193 http://doi.org/10.1002/aenm.202103193 .
Wang, J.; Jiang, X.; Wu, H., Li, J.; Yi, Y.; Feng, X.; Ma, Z.; Li, W.; Vandewal, K.; Tang, Z . Increasing donor-acceptor spacing for reduced voltage loss in organic solar cells . Nat. Commun. , 2021 . 12 6679 DOI: 10.1038/s41467-021-26995-1 http://doi.org/10.1038/s41467-021-26995-1 .
Jiang, X. D.; Yang, J. J.; Karuthedath, S; Li, J.; Lai, W.; Li, C.; Xiao, C.; Ye, L.; Mai, Z.; Tang, Z.; Laquai, F.; Li, W . Miscibility-controlled phase separation in double-cable conjugated polymers for single-component organic solar cells with efficiencies over 8% . Angew. Chem. Int. Ed. , 2020 . 59 21683 - 21692 . DOI: 10.1002/anie.202009272 http://doi.org/10.1002/anie.202009272 .
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