Citation: Jun Xu, Jinsheng Zhang, Daobin Yang, Kuibao Yu, Dandan Li, Zihao Xia, Ziyi Ge. Two star-shaped small molecule donors based on benzodithiophene unit for organic solar cells[J]. Chinese Chemical Letters, ;2022, 33(1): 247-251. doi: 10.1016/j.cclet.2021.06.023 shu

Two star-shaped small molecule donors based on benzodithiophene unit for organic solar cells

Jun Xu ^{a, c} ,
Jinsheng Zhang ^{a, b} ,
Daobin Yang ^{a, b, *} ,
Kuibao Yu ^a ,
Dandan Li ^{a, b} ,
Zihao Xia ^a ,
Ziyi Ge ^{a, b, *}

a.
Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China
b.
Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
c.
Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123, China

yangdaobin@nimte.ac.cn

geziyi@nimte.ac.cn

Received Date: 28 April 2021
Revised Date: 4 June 2021
Accepted Date: 7 June 2021
Available Online: 15 June 2021

Figures(5)

Star-shaped small molecules have attracted great attention for organic solar cells (OSCs) because they have three-dimensional charge-transport characteristics, strong light absorption capacities and easily tunable energy levels. Herein, three- and four-armed star-shaped small molecule donors, namely BDT-3Th and BDT-4Th, respectively, have been successfully designed and synthesized, which used benzodithiophene (BDT) as the central unit. The two star-shaped intermediates (2a and 2b) could be simultaneously obtained by one-step of Suzuki coupling, and 1, 2-dimethoxyethane played a key role in the Suzuki coupling. Both of them have excellent thermal stability, good solubility and broad absorption. Four-armed BDT-4Th shows a slightly higher extinction coefficient, a deeper HOMO energy level and an obviously better phase separation morphology when blended with Y6 than three-armed BDT-3Th. As a result, increased power conversion efficiency (PCE) of 5.83% is obtained in the BDT-4Th: Y6-based OSC devices, which is obviously higher than that of the BDT-3Th: Y6-based devices (PCE = 3.78%). To the best of our knowledge, this is the highest PCE among the BDT-based star-shaped donors-based OSCs. This result provides an effective strategy to obtain star-shaped small molecule donor materials for high efficient organic solar cells.
- Star-shaped molecules,
- Benzodithiophene,
- Suzuki coupling,
- Donor materials,
- Small molecules,
- Organic solar cells
1. [1]
  O. Inganas, Adv. Mater. 30(2018) 1800388. doi: 10.1002/adma.201800388
2. [2]
  S. Park, T. Kim, S. Yoon, et al., Adv. Mater. 32(2020) 2002217. doi: 10.1002/adma.202002217
3. [3]
  X. Xu, G. Zhang, Y. Li, et al., Chin. Chem. Lett. 30(2019) 809-825. doi: 10.1016/j.cclet.2019.02.030
4. [4]
  L. Shao, F. Tong, M. Zhu, et al., Chin. Chem. Lett. 31(2020) 2452-2458. doi: 10.1016/j.cclet.2020.03.036
5. [5]
  Q. Liu, Y. Jiang, K. Jin, et al., Sci. Bull. 65(2020) 272-275. doi: 10.1016/j.scib.2020.01.001
6. [6]
  Y. Lin, M.I. Nugraha, Y. Firdaus, et al., ACS Energy Lett. 5(2020) 3663-3671. doi: 10.1021/acsenergylett.0c01949
7. [7]
  L. Zhan, S. Li, X. Xia, et al., Adv. Mater. 33(2021) 2007231. doi: 10.1002/adma.202007231
8. [8]
  M. Zhang, L. Zhu, G. Zhou, et al., Nat. Commun. 12(2021) 309. doi: 10.1038/s41467-020-20580-8
9. [9]
  D. Yang, H. Sasabe, T. Sano, et al., ACS Energy Lett. 2(2017) 2021-2025. doi: 10.1021/acsenergylett.7b00608
10. [10]
  Q. Wei, W. Liu, M. Leclerc, et al., Sci. China Chem. 63(2020) 1352-1366. doi: 10.1007/s11426-020-9799-4
11. [11]
  W. Ye, Y. Yang, Z. Zhang, et al., Solar RRL 4(2020) 2000258. doi: 10.1002/solr.202000258
12. [12]
  J. Gao, J. Ge, R. Peng, et al., J. Mater. Chem. A 8(2020) 7405-7411. doi: 10.1039/D0TA01893G
13. [13]
  Y. Chang, J. Li, Y. Chang, et al., Chin. Chem. Lett. 32(2021) 2904-2908. doi: 10.1016/j.cclet.2021.03.067
14. [14]
  D. Hu, Q. Yang, H. Chen, et al., Energy Environ. Sci. 13(2020) 2134-2141. doi: 10.1039/D0EE00714E
15. [15]
  J. Qin, C. An, J. Zhang, et al., Sci. China Mater. 63(2020) 1142-1150. doi: 10.1007/s40843-020-1269-9
16. [16]
  L. Nian, Y. Kan, K. Gao, et al., Joule 4(2020) 2223-2236. doi: 10.1016/j.joule.2020.08.011
17. [17]
  Y.Q. Pan, G.Y. Sun, ChemSusChem 12(2019) 4570-4600. doi: 10.1002/cssc.201901013
18. [18]
  H. Wang, M. Li, Y. Liu, et al., J. Mater. Chem. C 7(2019) 819-825. doi: 10.1039/C8TC05332D
19. [19]
  X. Gao, Y. Wu, X. Song, et al., Dyes Pigments 188(2021) 109216. doi: 10.1016/j.dyepig.2021.109216
20. [20]
  J. Zhang, Y. Li, J. Huang, et al., J. Am. Chem. Soc. 139(2017) 16092-16095. doi: 10.1021/jacs.7b09998
21. [21]
  G. Cai, W. Wang, J. Zhou, et al., ACS Mater. Lett. 1(2019) 367-374. doi: 10.1021/acsmaterialslett.9b00253
22. [22]
  H. Wang, Q. Yue, T. Nakagawa, et al., J. Mater. Chem. A 7(2019) 4072-4083. doi: 10.1039/C8TA10710F
23. [23]
  L. Ye, S. Zhang, L. Huo, et al., Acc. Chem. Res. 47(2014) 1595-1603. doi: 10.1021/ar5000743
24. [24]
  H. Yao, L. Ye, H. Zhang, et al., Chem. Rev. 116(2016) 7397-7457. doi: 10.1021/acs.chemrev.6b00176
25. [25]
  Q. Wu, D. Zhao, A.M. Schneider, et al., J. Am. Chem. Soc. 138(2016) 7248-7251. doi: 10.1021/jacs.6b03562
26. [26]
  Z. Luo, T. Liu, W. Cheng, et al., J. Mater. Chem. C 6(2018) 1136-1142. doi: 10.1039/C7TC05261H
27. [27]
  Q. He, M. Shahid, J. Panidi, et al., J. Mater. Chem. C 7(2019) 6622-6629. doi: 10.1039/C9TC00905A
28. [28]
  J. Yuan, Y. Zhang, L. Zhou, et al., Joule 3(2019) 1140-1151. doi: 10.1016/j.joule.2019.01.004
29. [29]
  D. Yang, H. Sasabe, Y. Jiao, et al., J. Mater. Chem. A 4(2016) 18931-18941. doi: 10.1039/C6TA08684E
30. [30]
  N.K. Elumalai, A. Uddin, Energy Environ. Sci. 9(2016) 391-410. doi: 10.1039/C5EE02871J
31. [31]
  D. Yang, K. Yu, J. Xu, et al., J. Mater. Chem. A 9(2021) 10427-10436. doi: 10.1039/D1TA01680F
32. [32]
  M.C. Scharber, D. Mühlbacher, M. Koppe, et al., Adv. Mater. 18(2006) 789-794. doi: 10.1002/adma.200501717
33. [33]
  G. Yu, J. Gao, J.C. Hummelen, et al., Science 270(1995) 1789-1791. doi: 10.1126/science.270.5243.1789
34. [34]
  N.S. Sariciftci, L. Smilowitz, A.J. Heeger, et al., Science 258(1992) 1474-1476. doi: 10.1126/science.258.5087.1474
35. [35]
  T. Yan, W. Song, J. Huang, et al., Adv. Mater. 31(2019) 1902210. doi: 10.1002/adma.201902210
36. [36]
  T. Kumari, S.M. Lee, S.H. Kang, et al., Energy Environ. Sci. 10(2017) 258-265. doi: 10.1039/C6EE02851A
37. [37]
  H. Bin, Y. Yang, Z.G. Zhang, et al., J. Am. Chem. Soc. 139(2017) 5085-5094. doi: 10.1021/jacs.6b12826
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