
FOLLOWUS
a.Institute of Materials for Optoelectronics and New Energy, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan 430205, China
b.Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan 430074, China
c.Key Laboratory of Optoelectronic Chemical Materials and Devices (Ministry of Education), School of Optoelectronic Materials & Technology, Jianghan University, Wuhan 430056, China
witxgao@126.com; xgao@wit.edu.cn (X.G.)
mingshao@hust.edu.cn (M.S.)
able.ztliu@wit.edu.cn (Z.T.L.)
收稿日期:2024-12-07,
修回日期:2025-01-25,
录用日期:2025-02-10,
网络出版日期:2025-04-03,
纸质出版日期:2025-04-30
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Wu, Z. Y.; Liu, J. F.; Tong, X. Z.; Sun, Y. J.; Wang, X. C.; Yang, R. Q.; Gao, X.; Shao, M.; Li, P. C.; Liu, Z. T. Benzo[1,2-b:4,5-b’]difuran-based narrow bandgap polymers for efficient organic solar cells using perylene diimides-type nonfullerene acceptors. Chinese J. Polym. Sci. 2025, 43, 711–717
Zhen-Yu Wu, Jun-Feng Liu, Xin-Zhu Tong, et al. Benzo[1,2-b:4,5-b’]difuran-based Narrow Bandgap Polymers for Efficient Organic Solar Cells Using Perylene Diimides-type Nonfullerene Acceptors[J]. Chinese journal of polymer science, 2025, 43(5): 711-717.
Wu, Z. Y.; Liu, J. F.; Tong, X. Z.; Sun, Y. J.; Wang, X. C.; Yang, R. Q.; Gao, X.; Shao, M.; Li, P. C.; Liu, Z. T. Benzo[1,2-b:4,5-b’]difuran-based narrow bandgap polymers for efficient organic solar cells using perylene diimides-type nonfullerene acceptors. Chinese J. Polym. Sci. 2025, 43, 711–717 DOI: 10.1007/s10118-025-3318-6.
Zhen-Yu Wu, Jun-Feng Liu, Xin-Zhu Tong, et al. Benzo[1,2-b:4,5-b’]difuran-based Narrow Bandgap Polymers for Efficient Organic Solar Cells Using Perylene Diimides-type Nonfullerene Acceptors[J]. Chinese journal of polymer science, 2025, 43(5): 711-717. DOI: 10.1007/s10118-025-3318-6.
Two narrow-bandgap polymers
PBDF and PBDFCl
were synthesized
exhibiting red-shifted absorption
lower the highest occupied molecular orbital level and stronger aggregation than thiophene analogues. The power conversion efficiency of PBDFCl:Ph(PDI)
3
-based organic solar cells was 8.84%
much higher than PCE10-based ones (6.09%)
among the top performing ones that utilize PDI-based acceptors.
The development of narrow-bandgap polymer donors with complementary absorption and matched energy levels for perylene diimides (PDI)-based nonfullerene acceptors (NFAs) has received little attention. The high-lying highest occupied molecular orbital (HOMO) level and low degree of crystallinity of the star donor polymer PCE10 limit its application in PDI-based Organic solar cells (OSCs). In this study
two benzo[1
2-b:4
5-b′
]
difuran (BDF)-based narrow-bandgap polymer donors
PBDF and PBDFCl
were synthesized to improve the photovoltaic performance of PDI-based OSCs. The smaller BDF moiety with higher electronegativity endows the resulting polymers with stronger aggregation and lower HOMO energy levels. The power conversion efficiency (PCE) value of the PBDF:Ph(PDI)
3
-based OSCs was 7.24%
which is much higher than that of PCE10-based OSCs (6.09%). Further chlorination of the conjugated side chain elevated the PCE to 8.84%
which is 1.4 times higher than that of PCE10-based OSCs. These results demonstrate the significant contribution of designing novel narrow-bandgap polymer donors to boost the PCE of PDI-based OSCs and highlight the importance of matching the aggregation behaviors of polymeric donor materials with that of NFAs.
Ding, P.; Yang, D.; Yang, S. ; Ge, Z. Stability of organic solar cells: toward commercial applications. Chem. Soc. Rev. 2024 , 53 , 2350−2387..
Yuan, X.; Zhang, B.; Li, Y.; Zhao, F.; Wei, W.; Zhang, Y.; Li, J.; Tian, Y.; Ma, Z.; Tang, Z.; Liu, Z.; Huang, F.; Cao, Y.; Duan, C. Halogen-free wide band gap polymer donors based on dicyanobithiophene for efficient organic solar cells. ACS App. Mater. Interfaces 2025 , 17 , 6659−6667..
Chen, Q.; Gao, Y.; Dong, J.; Yang, Y.; Huang, H.; Aniés, F.; Bian, Z.; Xu, X.; Li, C.; Yao, C.; Heeney, M.; Li, W.; Bo, Z. Alkoxy modification of the terminal group in nonfullerene acceptors to achieve efficient ternary organic solar cells with a high open-circuit voltage. Adv. Funct. Mater . 2025 , Doi: 10.1002/adfm.202423287..
Zhou, H.; Zhang, L.; Ma, X.; Xibei, Y.; Zheng, Y.; Liu, Z.; Gao, X.; Zhang, J.; Liu, Z.; Zhang, F. Approaching 18% efficiency of ternary layer-by-layer polymer solar cells with alloyed acceptors. Chem. Eng. J. 2023 , 462 , 142327..
Gao, J.; Zhu, X.; Bao, H.; Feng, J.; Gao, X.; Liu, Z.; Ge, Z. Latest progress on fully non-fused electron acceptors for high-performance organic solar cells. Chinese Chem. Lett. 2023 , 34 , 107968..
Gao, X.; Ma, X.; Liu, Z.; Gao, J.; Qi, Q.; Yu, Y.; Gao, Y.; Ma, Z.; Ye, L.; Min, J.; Wen, J.; Gao, J.; Zhang, F.; Liu, Z. Novel third components with (thio)barbituric acid as the end groups improving the efficiency of ternary solar cells. ACS Appl. Mater. Interfaces 2022 , 14 , 23701−23708..
Hou, J.; Inganäs, O.; Friend, R. H.; Gao, F. Organic solar cells based on non-fullerene acceptors. Nat. Mater. 2018 , 17 , 119−128..
Aldrich, T. J.; Matta, M.; Zhu, W.; Swick, S. M.; Stern, C. L.; Schatz, G. C.; Facchetti, A.; Melkonyan, F. S.; Marks, T. J. Fluorination effects on indacenodithienothiophene acceptor packing and electronic structure, end-group redistribution, and solar cell photovoltaic response. J. Am. Chem. Soc. 2019 , 141 , 3274−3287..
Zhang, G.; Zhao, J.; Chow, P. C. Y.; Jiang, K.; Zhang, J.; Zhu, Z.; Zhang, J.; Huang, F.; Yan, H. Nonfullerene acceptor molecules for bulk heterojunction organic solar cells. Chem. Rev. 2018 , 118 , 3447−3507..
Nielsen, C. B.; Holliday, S.; Chen, H. Y.; Cryer, S. J.; McCulloch, I. Non-fullerene electron acceptors for use in organic solar cells. Acc. Chem. Res. 2015 , 48 , 2803−2812..
Swick, S. M.; Gebraad, T.; Jones, L.; Fu, B.; Aldrich, T. J.; Kohlstedt, K. L.; Schatz, G. C.; Facchetti, A.; Marks, T. J. Building blocks for high-efficiency organic photovoltaics: interplay of molecular, crystal, and electronic properties in post-fullerene ITIC ensembles. ChemPhysChem 2019 , 20 , 2608−2626..
Wang, J.; Zhan, X. Rylene diimide electron acceptors for organic solar cells. Trends Chem. 2019 , 1 , 869−881..
Liu, Z.; Wu, Y.; Zhang, Q.; Gao, X. Non-fullerene small molecule acceptors based on perylene diimides. J. Mater. Chem. A 2016 , 4 , 17604−17622..
Gao, X.; Jing, W.; Wang, Y.; Xu, X.; Zhang, L.; Chen, Z.; Wen, J.; Gao, J.; Peng, Q.; Liu, Z. Efficient perylene-diimides-based nonfullerene acceptors with triazine cores synthesized via a simple nucleophilic substitution reaction. Sci. China Mater. 2023 , 66 , 2159−2168..
Sisto, T. J.; Zhong, Y.; Zhang, B.; Trinh, M. T.; Miyata, K.; Zhong, X.; Zhu, X. Y.; Steigerwald, M. L.; Ng, F.; Nuckolls, C. Long, Atomically precise donor-acceptor cove-edge nanoribbons as electron acceptors. J. Am. Chem. Soc. 2017 , 139 , 5648−5651..
Liu, J.; Chen, S.; Qian, D.; Gautam, B.; Yang, G.; Zhao, J.; Bergqvist, J.; Zhang, F.; Ma, W.; Ade, H.; Inganäs, O.;Gundogdu, K.; Gao, F.; Yan, H. Fast charge separation in a non-fullerene organic solar cell with a small driving force. Nat. Energy 2016 , 1 , 16089..
Gao, X.; Wu, X.; Wu, Z.; Gao, J.; Liu, Z. J. S. C. C. Organic solar cells based on molecular perylene diimides-type nonfullerene acceptors: achievements, challenges and the future. Sci. China Chem . 2025 , Doi: 10.1007/s11426-024-2406-9..
Gao, X.; Sun, F.; Tong, X.; Zheng, X.; Wang, Y.; Xiao, C.; Li, P.; Yang, R.; Wang, X.; Liu, Z. Efficient soluble PTCBI-type non-fullerene acceptor materials for organic solar cells. Front. Optoelectron. 2023 , 16 , 8..
Sun, Y.J.; Wang, Y. N.; Sun, F. B.; Zhou, R. Z.; Gao, X.; Zhang, Q.; Gao, J. H.; Liu, Z. T. Biphenyl core boosts the photovoltaic performance of ether-bonded perylene diimides based nonfullerene acceptors. Dyes Pigment 2025 , 239 , 112771..
Gao, J.; Zhang, L.; Shen, H.; Sun, F.; Gao, X.; Sun, Y.; Tong, X.; Wen, J.; Li, P.; Wu, D.; Xia, J.; Liu, Z. Chlorinated perylene monoimide monoanhydrate synthesized via hydrolysis and its application in organic solar cells. Chinese J. Polym. Sci. 2023 , 41 , 1686−1694..
Zhang, L.; Chen, Z.; Sun, F.; Wang, Y.; Bao, H.; Gao, X.; Liu, Z. Progress of monomeric perylene diimide derivatives as non-fullerene acceptors for organic solar cells. J. Electron. Mater. 2022 , 51 , 4224−4237..
Liao, S.; Jhuo, H.; Cheng, Y.; Chen, S. Fullerene derivative-doped zinc oxide nanofilm as the cathode of inverted polymer solar cells with low-bandgap polymer (PTB7-Th) for high performance. Adv. Mater. 2013 , 25 , 4766−4771..
Zhang, X.; Lu, Z.; Ye, L.; Zhan, C.; Hou, J.; Zhang, S.; Jiang, B.; Zhao, Y.; Huang, J.; Zhang, S.; Liu, Y.; Shi, Q.; Liu, Y.; Yao, J. A potential perylene diimide dimer-based acceptor material for highly efficient solution-processed non-fullerene organic solar cells with 4.03% efficiency. Adv. Mater. 2013 , 25 , 5791−5797..
Zhong, Y.; Trinh, M. T.; Chen, R.; Purdum, G. E.; Khlyabich, P. P.; Sezen, M.; Oh, S.; Zhu, H.; Fowler, B.; Zhang, B.; Wang, W.; Nam, C.; Sfeir, M. Y.; Black, C. T.; Steigerwald, M. L.; Loo, Y.; Ng, F.; Zhu, X. Y.; Nuckolls, C. Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells. Nat. Commun. 2015 , 6 , 8242..
Zhong, H.; Wu, C.; Li, C.; Carpenter, J.; Chueh, C.; Chen, J.; Ade, H.; Jen, A. K. Rigidifying nonplanar perylene diimides by ring fusion toward geometry-tunable acceptors for high-performance fullerene-free solar cells. Adv. Mater. 2016 , 28 , 951−958..
Hwang, Y. J.; Courtright, B. A. E.; Ferreira, A. S.; Tolbert, S. H.; Jenekhe, S. A. 7.7% Efficient all-polymer solar cells. Adv. Mater . 2015 , 27 , 4578−4584..
Yao, Z.; Liao, X.; Gao, K.; Lin, F.; Xu, X.; Shi, X.; Zuo, L.; Liu, F.; Chen, Y.; Jen, A. K. Y. Dithienopicenocarbazole-based acceptors for efficient organic solar cells with optoelectronic response over 1000 nm and an extremely low energy loss. J. Am. Chem. Soc. 2018 , 140 , 2054−2057..
Gao, X.; Tong, X.; Xu, M.; Zhang, L.; Wang, Y.; Li u, Z.; Yang, L.; Gao, J.; Shao, M.; Liu, Z. Chlorinated narrow bandgap polymer suppresses non-radiative recombination energy loss enabling perylene diimides-based organic solar cells exceeding 10% efficiency. Small 2023 , 19 , 2208217..
Deng, M.; Zhang, G.; Yu, L.; Xu, X.; Peng, Q. Noncovalent interaction enables planar and efficient propeller-like perylene diimide acceptors for polymer solar cells. Chem. Eng. J. 2021 , 426 , 131910..
Zhang, G.; Feng, J.; Xu, X.; Ma, W.; Li, Y.; Peng, Q. Perylene diimide-based nonfullerene polymer solar cells with over 11% efficiency fabricated by smart molecular design and supramolecular morphology optimization. Adv. Mater. 2019 , 29 , 1906587..
Zhang, G.; Xu, X.; Lee, Y. W.; Woo, H. Y.; Li, Y.; Peng, Q. 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. Adv. Funct. Mater. 2019 , 29 , 1902079..
Chen, S.; Meng, D.; Huang, J.; Liang, N.; Li, Y.; Liu, F.; Yan, H.; Wang, Z. Symmetry-induced orderly assembly achieving high-performance perylene diimide-based nonfullerene organic solar cells. CCS Chem. 2021 , 3 , 78−84..
Cui, C.; Wong, W. Effects of alkylthio and alkoxy side chains in polymer donor materials for organic solar cells. Macromol. Rapid Commum. 2016 , 37 , 287−302..
Zhang, Z.; Li, Y. Side-chain engineering of high-efficiency conjugated polymer photovoltaic materials. Sci. China Chem. 2015 , 58 , 192−209..
Cui, C.; Wong, W. Y.; Li, Y. Improvement of open-circuit voltage and photovoltaic properties of 2D-conjugated polymers by alkylthio substitution. Energ. Environ. Sci. 2014 , 7 , 2276−2284..
Rühle, S. Tabulated values of the shockley–queisser limit for single junction solar cells. Sol. Energy 2016 , 130 , 139−147..
Huang, X.; Oh, J.; Cheng, Y.; Huang, B.; Ding, S.; He, Q.; Wu, F.; Yang, C.; Chen, L.; Chen, Y. Narrow band-gap materials with overlapping absorption simultaneously increase the open circuit voltage and average visible transmittance of semitransparent organic solar cells. J. Mater. Chem. A 2021 , 9 , 5711−5719..
Cui, C.; Li, Y. High-performance conjugated polymer donor materials for polymer solar cells with narrow-bandgap nonfullerene acceptors. Energ. Environ. Sci. 2019 , 12 , 3225−3246..
Bao, H.; Yang, Z.; Zhao, Y.; Gao, X.; Tong, X.; Wang, Y.; Sun, F.; Gao, J.; Li, W.; Liu, Z. Chlorinated effects of double-cable conjugated polymers on the photovoltaic performance in single-component organic solar cells. Chinese J. Polym. Sci. 2023 , 41 , 187−193..
Liu, Z.; Gao, Y.; Dong, J.; Yang, M.; Liu, M.; Zhang, Y.; Wen, J.; Ma, H.; Gao, X.; Chen, W.; Shao, M. Chlorinated wide-bandgap donor polymer enabling annealing free nonfullerene solar cells with the efficiency of 11.5%. J. Phys. Chem. Lett. 2018 , 9 , 6955−6962..
Zhu, W.; Alzola, J. M.; Aldrich, T. J.; Kohlstedt, K. L.; Zheng, D.; Hartnett, P. E.; Eastham, N. D.; Huang, W.; Wang, G.; Young, R. M.; Schatz, G. C.; Wasielewski, M. R.; Facchetti, A.; Melkonyan, F. S.; Marks, T. J. Fluorine tuning of morphology, energy loss, and carrier dynamics in perylenediimide polymer solar cells. ACS Energy Lett. 2019 , 4 , 2695−2702..
Gao, X.; Shen, J.; Hu, B.; Tu, G. A straightforward synthesis of chlorine-bearing donor-acceptor alternating copolymers with deep frontier orbital levels. Macromol. Chem. Phys. 2014 , 215 , 1388−1395..
Gao, X.; Zhang, Y.; Fang, C.; Cai, X.; Hu, B.; Tu, G. Efficient deep-red electroluminescent donor-acceptor copolymers based on 6,7-dichloroquinoxaline. Org. Electron. 2017 , 46 , 276−282..
Zhang, Y.; Gao, X.; Li, J.; Tu, G. Highly selective palladium-catalyzed stille coupling reaction toward chlorine-containing NIR electroluminescent polymers. J. Mater. Chem. C 2015 , 3 , 7463−7468..
Zhang, S.; Qin, Y.; Zhu, J.; Hou, J. Over 14% efficiency in polymer solar cells enabled by a chlorinated polymer donor. Adv. Mater. 2018 , 30 , 1800868..
Liu, W.; Li, W.; Yao, J.; Zhan, C. Achieving high short-circuit current and fill-factor via increasing quinoidal character on nonfullerene small molecule acceptor. Chin. Chem. Lett. 2018 , 29 , 381−384..
Xie, D.; Liu, T.; G ao, W.; Zhong, C.; Huo, L.; Luo, Z.; Wu, K.; Xiong, W.; Liu, F.; Sun, Y.; Yang, C. A novel thiophene-fused ending group enabling an excellent small molecule acceptor for high-performance fullerene-free polymer solar cells with 11.8% efficiency. Solar RRL 2017 , 1 , 1700044..
Chen, X.; Liu, B.; Zou, Y.; Xiao, L.; Guo, X.; He, Y.; Li, Y. A new benzo[1,2-b:4,5-b′ ] difuran-based copolymer for efficient polymer solar cells. J. Mater. Chem. 2012 , 22 , 17724−17731..
Huo, L.; Huang, Y.; Fan, B.; Guo, X.; Jing, Y.; Zhang, M.; Li, Y.; Hou, J. Synthesis of a 4,8-dialkoxy-benzo[1,2-b:4,5-b′ ] difuran unit and its application in photovoltaic polymer. Chem. Commun. 2012 , 48 , 3318−3320..
Zhao, Z.; Nie, H.; Ge, C.; Cai, Y.; Xiong, Y.; Qi, J.; Wu, W.; Kwok,R. T. K.; Gao, X.; Qin, A.; Lam, J. W. Y.; Tang, B. Z. Furan is superior to thiophene: a furan-cored AIEgen with remarkable chromism and OLED performance. Adv. Sci. 2017 , 4 , 1700005..
Gao, Y.; Wang, Z.; Zhang, J.; Zhang, H.; Lu, K.; Guo, F.; Yang, Y.; Zhao, L.; Wei, Z.; Zhang, Y. Two-dimensional benzo[1,2-b:4,5-b′ ] difuran-based wide bandgap conjugated polymers for efficient fullerene-free polymer solar cells. J. Mater. Chem. A 2018 , 6 , 4023−4031..
Huang, P.; Du, J.; Gunathilake, S. S.; Rainbolt, E. A.; Murphy, J. W.; Black, K. T.; Barrera, D.; Hsu, J. W. P.; Gnade, B. E.; Stefan, M. C.; Biewer, M. C. Benzodifuran and benzodithiophene donor-acceptor polymers for bulk heterojunction solar cells. J. Mater. Chem. A 2015 , 3 , 6980−6989..
Qiao, S.; Li, X.; Wang, H.; Zhang, B.; Li, Z.; Zhao, J.; Chen, W.; Yang, R. Temperature-dependent and aggregation-breaking strategy for benzodifuran-constructed organic solar cells. Solar RRL 2019 , 3 , 1900159..
Li, X.; Duan, X.; Liang, Z.; Yan, L.; Yang, Y.; Qiao, J.; Hao, X.; Zhang,C.; Zhang, J.; Li, Y.; Huang, F.; Sun, Y. Benzo[1,2-b:4,5-b’ ] difuran based polymer donor for high-efficiency ( > 16%) and stable organic solar cells. Adv. Energy Mater. 2022 , 12 , 2103684..
Huo, L.; Liu, T.; Fan, B.; Zhao, Z.; Sun, X.; Wei, D.; Yu, M.; Liu, Y.; Sun, Y. Organic solar cells based on a 2D benzo[1,2-b:4,5-b′ ] difuran-conjugated polymer with high-power conversion efficiency. Adv. Mater. 2015 , 27 , 6969−6975..
Warnan, J.; Cabanetos, C.; Labban, A. E.; Hansen, M. R.; Tassone, C. J.; Toney, M. F.; Beaujuge, P. M. J. A. M. Ordering effects in benzo[1,2-b:4,5-b′ ] difuran-thieno[3,4-c ] pyrrole-4,6-dione polymers with > 7% solar cell efficiency. Adv. Mater. 2014 , 26 , 4257−4362..
Chen, W.; Du, Z.; Xiao, M.; Zhang, J.; Yang, C.; Han, L.; Bao, X.; Yang, R. High-performance small molecule/polymer ternary organic solar cells based on a layer-by-layer process. ACS Appl. Mater. Interfaces 2015 , 7 , 23190−23196..
Gandini, A. The irruption of polymers from renewable resources on the scene of macromolecular science and technology. Green Chem. 2011 , 13 , 1061−1083..
Li, X.; Huang, G.; Chen, W.; Jiang, H.; Qiao, S.; Yang, R. Size effect of two-dimensional conjugated space in photovoltaic polymers’ side chain: balancing phase separation and charge transport. ACS Appl. Mater. Interfaces 2020 , 12 , 16670−16678..
Huo, L.; Li, Z.; Guo, X.; Wu, Y.; Zhang, M.; Ye, L. W.; Zhang, S.; Hou, J. J. P. C. Benzodifuran-alt-thienothiophene based low band gap copolymers: substituent effects on their molecular energy levels and photovoltaic properties. Polym. Chem. 2013 , 4 , 3047−3056..
Zhang, C.; Mahadevan, S.; Yuan, J.; Ho, J. K. W.; Gao, Y.; Liu, W.; Zhong, H.; Yan, H.; Zou, Y.; Tsang, S.; So, S. K. Unraveling urbach tail effects in high-performance organic photovoltaics: dynamic vs static disorder. ACS Energy Lett. 2022 , 7 , 1971−1979..
Tang, M. L.; Oh, J. H.; Reichardt, A. D.; Bao, Z. Chlorination: a general route toward electron transport in organic semiconductors. J. Am. Chem. Soc. 2009 , 131 , 3733−3740..
Meng, D.; Fu, H.; Xiao, C.; Meng, X.; Winands, T.; Ma, W.; Wei, W.; Fan, B.; Huo, L.; Doltsinis, N. L.; Li, Y.; Sun, Y.; Wang, Z. Three-bladed rylene propellers with three-dimensional network assembly for organic electronics. J. Am. Chem. Soc. 2016 , 138 , 10184−10190..
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