Citation: Ruochuan Liao, Changquan Tang, Yunlong Ma, Qingdong Zheng. Impact of regio-isomeric monochlorinated end groups on packing mode, miscibility, and photovoltaic performance of asymmetric selenophene-fused M-series acceptors[J]. Chinese Chemical Letters, ;2023, 34(12): 108448. doi: 10.1016/j.cclet.2023.108448 shu

Impact of regio-isomeric monochlorinated end groups on packing mode, miscibility, and photovoltaic performance of asymmetric selenophene-fused M-series acceptors

Ruochuan Liao ^{a, c} ,
Changquan Tang ^a ,
Yunlong Ma ^a ,
Qingdong Zheng ^{a, b, *,}

a.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
b.
State Key Laboratory of Coordination Chemistry, College of Engineering and Applied Sciences, Nanjing University, Nanjing 210023, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

qingdongzheng@fjirsm.ac.cn

Received Date: 31 January 2023
Revised Date: 9 April 2023
Accepted Date: 11 April 2023
Available Online: 13 April 2023

Figures(5)

Optimal bulk-heterojunction (BHJ) morphology is crucial for efficient charge transport and good photovoltaic performance in organic solar cells (OSCs). Yet, the correlation between chemical structures of nonfullerene acceptors (NFAs) and molecular interaction in the BHJ blends remains opaque. Herein, we study three isomeric NFAs referred to as MQ1-x (x = β, γ, or δ) that shared an asymmetric selenophene-fused heteroheptacene backbone end-capped by two monochlorinated end groups. Remarkably, miscibility between the polymer donor of PM6 and MQ1-x successively elevates as the chlorine atoms move from β-, to γ-, to δ-position of terminals. Combined with the varied molecular crystallinity of these NFAs, diverse BHJ morphologies are observed in their blend films. As a result, the MQ1-δ-based devices present the highest PCE of 12.08% owing to the efficient charge dissociation and transport induced by the compact molecular packing and optimal BHJ morphology. Our investigation provides a new insight in the material design that has a good balance in molecular packing and film morphology for high-performance OSCs.
- Organic solar cells,
- Miscibility,
- Noncovalent interaction,
- Chlorinated isomers,
- Molecular packing
1. [1]
  P. Cheng, G. Li, X.W. Zhan, Y. Yang, Nat. Photonics 12 (2018) 131–142. doi: 10.1038/s41566-018-0104-9
2. [2]
  C.B. Nielsen, S. Holliday, H.Y. Chen, et al., Acc. Chem. Res. 48 (2015) 2803–2812. doi: 10.1021/acs.accounts.5b00199
3. [3]
  T. Ameri, P. Khoram, J. Min, C.J. Brabec, Adv. Mater. 25 (2013) 4245–4266. doi: 10.1002/adma.201300623
4. [4]
  Y. Liu, B. Li, C.Q. Ma, et al., Sci. China Chem. 65 (2022) 224–268. doi: 10.1007/s11426-021-1180-6
5. [5]
  C.Z. Sun, X. Lai, T. Rehman, et al., J. Mater. Chem. C 10 (2022) 17174–17181. doi: 10.1039/d2tc03701g
6. [6]
  S. Luo, F. Bai, J. Zhang, et al., Nano Energy 98 (2022) 107281. doi: 10.1016/j.nanoen.2022.107281
7. [7]
  Y. Zhang, Y. Ji, Y. Zhang, et al., Adv. Funct. Mater. 32 (2022) 2205115. doi: 10.1002/adfm.202205115
8. [8]
  X. Yuan, Y. Zhao, D. Xie, et al., Joule 6 (2022) 647–661. doi: 10.1016/j.joule.2022.02.006
9. [9]
  H. Wang, H. Lu, Y.N. Chen, et al., Adv. Mater. 34 (2022) 2105483. doi: 10.1002/adma.202105483
10. [10]
  W. Liu, J. Yuan, C. Zhu, et al., Sci. China Chem. 65 (2022) 1374–1382. doi: 10.1007/s11426-022-1281-0
11. [11]
  R. Sun, Y. Wu, X. Yang, et al., Adv. Mater. 34 (2022) 2110147. doi: 10.1002/adma.202110147
12. [12]
  L. Zhan, S. Li, Y. Li, et al., Joule 6 (2022) 662–675. doi: 10.1016/j.joule.2022.02.001
13. [13]
  L. Yang, H. Wang, J. Cao, et al., Chem. Eng. J. 427 (2022) 131942. doi: 10.1016/j.cej.2021.131942
14. [14]
  Z. Bi, H.B. Naveed, H. Wu, et al., Adv. Energy Mater. 12 (2022) 2103735. doi: 10.1002/aenm.202103735
15. [15]
  K. Xian, S. Zhang, Y. Xu, et al., Sci. China Chem. 66 (2023) 202–215. doi: 10.1007/s11426-022-1394-y
16. [16]
  X. Jiang, J. Yang, S. Karuthedath, et al., Angew. Chem. Int. Ed. 59 (2020) 21683–21692. doi: 10.1002/anie.202009272
17. [17]
  Z. Zhou, W. Liu, G. Zhou, et al., Adv. Mater. 32 (2020) 1906324. doi: 10.1002/adma.201906324
18. [18]
  Y. Lin, J. Wang, Z.G. Zhang, et al., Adv. Mater. 27 (2015) 1170. doi: 10.1002/adma.201404317
19. [19]
  S.M. Swick, W. Zhu, M. Matta, et al., Proc. Natl. Acad. Sci. U. S. A. 115 (2018) E8341–E8348.
20. [20]
  X. Li, H. Huang, I. Angunawela, et al., Adv. Funct. Mater. 30 (2020) 1906855. doi: 10.1002/adfm.201906855
21. [21]
  Y.L. Ma, D.D. Cai, S. Wan, et al., Natl. Sci. Rev. 7 (2020) 1886–1895. doi: 10.1093/nsr/nwaa189
22. [22]
  C. Tang, X. Ma, J.Y. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 19314–19323. doi: 10.1002/anie.202105861
23. [23]
  J. Yuan, Y.Q. Zhang, L.Y. Zhou, et al., Joule 3 (2019) 1140–1151. doi: 10.1016/j.joule.2019.01.004
24. [24]
  L. Zhu, M. Zhang, J. Xu, et al., Nat. Mater. 21 (2022) 656. doi: 10.1038/s41563-022-01244-y
25. [25]
  D.H. Li, X. Zhang, D. Liu, T. Wang, J. Mater. Chem. A 8 (2020) 15607–15619. doi: 10.1039/d0ta03703f
26. [26]
  X. Liao, H. Pei, H. Zhao, et al., Chem. Eng. J. 435 (2022) 135020. doi: 10.1016/j.cej.2022.135020
27. [27]
  J. Xu, F. Lin, L. Zhu, et al., Adv. Energy Mater. 12 (2022) 2201338. doi: 10.1002/aenm.202201338
28. [28]
  X. Wang, A. Tang, J. Yang, et al., Sci. China Chem. 63 (2020) 1666–1674. doi: 10.1007/s11426-020-9840-x
29. [29]
  C. Yang, Q. An, H.R. Bai, et al., Angew. Chem. Int. Ed. 60 (2021) 19241–19252. doi: 10.1002/anie.202104766
30. [30]
  H. Lu, H. Jin, H. Huang, et al., Adv. Funct. Mater. 31 (2021) 2103445. doi: 10.1002/adfm.202103445
31. [31]
  G. Han, T. Hu, Y. Yi, Adv. Mater. 32 (2020) 2000975. doi: 10.1002/adma.202000975
32. [32]
  Q. Tu, W. Zheng, Y. Ma, et al., CCS Chem. 5 (2023) 455–468. doi: 10.31635/ccschem.022.202101524
33. [33]
  S. Feng, M. Li, N. Tang, et al., ACS Appl. Mater. Interfaces 12 (2020) 4638–4648. doi: 10.1021/acsami.9b18076
34. [34]
  Y. Pan, X. Zheng, J. Guo, et al., Adv. Funct. Mater. 32 (2022) 2108614. doi: 10.1002/adfm.202108614
35. [35]
  S.M. Swick, J.M. Alzola, V.K. Sangwan, et al., Adv. Energy Mater. 10 (2020) 2000635. doi: 10.1002/aenm.202000635
36. [36]
  S. Dai, F. Zhao, Q. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 1336–1343. doi: 10.1021/jacs.6b12755
37. [37]
  C. Yang, S. Zhang, J. Ren, et al., Chin. Chem. Lett. 32 (2021) 2274–2278. doi: 10.1016/j.cclet.2021.03.006
38. [38]
  H.F. Yao, J.W. Wang, Y. Xu, et al., Acc. Chem. Res. 53 (2020) 822–832. doi: 10.1021/acs.accounts.0c00009
39. [39]
  L. Ye, H. Hu, M. Ghasemi, et al., Nat. Mater. 17 (2018) 253–260. doi: 10.1038/s41563-017-0005-1
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