Citation: Liu Jikang, Jiang Pengfei, Wang Yao, Tu Guoli. Synthesis of two A-B-C type conjugated amphiphilic triblock fullerene derivatives and their application in organic solar cells[J]. Chinese Chemical Letters, ;2020, 31(1): 119-124. doi: 10.1016/j.cclet.2019.05.023 shu

Synthesis of two A-B-C type conjugated amphiphilic triblock fullerene derivatives and their application in organic solar cells

Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan 430074, China

tgl@hust.edu.cn

Received Date: 1 April 2019
Revised Date: 19 April 2019
Accepted Date: 13 May 2019
Available Online: 13 January 2019

Figures(5)

Two A-B-C type conjugated amphiphilic triblock fullerene derivatives C₆₀-2HMTPB and C₆₀-2EHTPB were obtained in multi steps synthesis with three different blocks, and the amphiphilic diblock molecular C₆₀-4TPB was also preferred as a reference. When as modifying layer on zinc oxide (ZnO), the three fullerene derivatives can all reduce the work function of ZnO via modulation of the interfacial dipoles and lead a better electrical coupling. As introducing treatment of toluene, the obvious self-assembly of fullerene derivatives were observed, which were supported by X-ray diffraction and contact angle of water measurement. Base on PTB7-Th:PC₇₁BM system, the inverted organic solar cells devices with structure of ITO/ZnO/fullerene derivatives/PTB7-Th:PC₇₁BM/MoO₃/Al got power conversion efficiencies of 8.62%, 8.83% and 9.00% for C₆₀-4TPB, C₆₀-2HMTPB and C₆₀-2EHTPB, respectively, compared 8.13% of devices with bare ZnO. The result of conjugated amphiphilic triblock fullerene derivatives provides a straightforward approaching by simultaneously modulating the morphology and interfacial work function of ZnO, which can also lead high performance in optoelectronic devices.
- Amphiphilic triblock fullerene derivatives,
- Interfacial dipoles,
- Interface compatibility,
- Self-assembly,
- Water contact angle
1. [1]
  L. Verheyen, B. Timmermans, G. Koeckelberghs, et al., Macromolecules 51 (2018) 6421-6429. doi: 10.1021/acs.macromol.8b01302
2. [2]
  M. Nasiri, D. Saxon, T. Reineke, et al., Macromolecules 51 (2018) 2456-2465. doi: 10.1021/acs.macromol.7b02248
3. [3]
  D. Ndaya, R. Bosire, L. Mahajan, et al., Polym. Chem. 9 (2018) 1404-1411. doi: 10.1039/C7PY02127E
4. [4]
  Y. Qi, B. Li, Y. Wang, et al., Polym. Chem. 8 (2017) 6964-6971. doi: 10.1039/C7PY01680H
5. [5]
  A. Ding, G. Lu, H. Guo, et al., Polym. Chem. 8 (2017) 7537-7545. doi: 10.1039/C7PY01407D
6. [6]
  Q. Xu, Y. Zhang, X. Li, et al., Polym. Chem. 9 (2018) 4908-4916. doi: 10.1039/C8PY01053F
7. [7]
  D. Lye, Y. Xia, M. Wong, et al., Macromolecules 50 (2017) 4244-4255. doi: 10.1021/acs.macromol.7b00169
8. [8]
  G. Zaldivar, M. Samad, M. Conda-Sheridan, et al., Soft Matter 14 (2018) 3171-3181. doi: 10.1039/C8SM00096D
9. [9]
  J. Palacios, A. Tercjak, G. Liu, et al., Macromolecules 50 (2017) 7268-7281. doi: 10.1021/acs.macromol.7b01576
10. [10]
  P. Zhou, Y. Liu, L. Niu, et al., Polym. Chem. 6 (2015) 2934-2944. doi: 10.1039/C4PY01804D
11. [11]
  W. Deng, K. Gao, J. Yan, et al., ACS Appl. Mater. Interfaces 10 (2018) 8141-8147. doi: 10.1021/acsami.7b17546
12. [12]
  Y. Shin, C. Song, W. Lee, et al., Macromol. Rapid Commun. 38 (2017) 1700016. doi: 10.1002/marc.201700016
13. [13]
  C. Jangu, J. Wang, D. Wang, et al., J. Mater. Chem. C 3 (2015) 3891-3901.
14. [14]
  J. Li, J. Liu, G. Tu, Solar Energy 181 (2019) 405-413. doi: 10.1016/j.solener.2019.01.066
15. [15]
  D. Zhou, S. Xiong, L. Chen, et al., Chem. Commun. 54 (2018) 563-566. doi: 10.1039/C7CC08604K
16. [16]
  Y. Yin, Y. Zhang, L. Zhao, et al., Macromol. Rapid Commun. 39 (2018) e1700697. doi: 10.1002/marc.201700697
17. [17]
  M. Neophytou, D. Bryant, S. Lopatin, et al., Macromol. Rapid Commun. 39 (2018) e1700820. doi: 10.1002/marc.201700820
18. [18]
  X. Li, S. Liu, K. Fan, et al., Adv. Energy Mater. 8 (2018) 1800101.
19. [19]
  Z. Jiang, H. Li, Z. Wang, et al., Macromol. Rapid Commun. 39 (2018) e1700872. doi: 10.1002/marc.201700872
20. [20]
  H. Han, J. Seo, M. Song, et al., J. Mater. Chem. A 6 (2018) 7480-7487. doi: 10.1039/C8TA00147B
21. [21]
  X. Cai, T. Yua, X. Liu, et al., ACS Appl. Mater. Interfaces 9 (2017) 36082-36089. doi: 10.1021/acsami.7b10399
22. [22]
  Y. Cheng, F. Cao, W. Lin, et al., Chem. Mater. 23 (2011) 1512-1518. doi: 10.1021/cm1032404
23. [23]
  M. Mahmud, N. Elumalai, M. Upama, et al., Nanoscale 10 (2018) 773-790. doi: 10.1039/C7NR06812C
24. [24]
  F. Wang, Y. Zhou, X. Pan, et al., Phys. Chem. Chem. Phys. 20 (2018) 6959-6969. doi: 10.1039/C7CP06909J
25. [25]
  Y. Tan, L. Chen, F. Wu, et al., Macromolecules 51 (2018) 8197-8204. doi: 10.1021/acs.macromol.8b01490
26. [26]
  J. Cao, B. Wu, R. Chen, et al., Adv. Mater. 30 (2018) 1705596. doi: 10.1002/adma.201705596
27. [27]
  Y. Cui, H. Yao, B. Gao, et al., J. Am. Chem. Soc. 139 (2017) 7302-7309. doi: 10.1021/jacs.7b01493
28. [28]
  S. Lu, H. Lin, S. Zhang, et al., Adv. Energy Mater. 7 (2017) 1701164.
29. [29]
  Y. Chao, Y. Huang, J. Chang, et al., J. Mater. Chem. A 3 (2015) 20382-20388. doi: 10.1039/C5TA05057J
30. [30]
  X. Zeng, J. Zhu, L. Yang, et al., J. Electron. Chem. 838 (2019) 94-100. doi: 10.1016/j.jelechem.2019.02.051
31. [31]
  Z. Zhang, X. Zhu, Chem. Mater. 5 (2018) 182-189.
32. [32]
  N. Tummala, S. Aziz, V. Coropceanu, et al., J. Mater. Chem. C 6 (2018) 3642-3650.
33. [33]
  S. Nam, J. Seo, M. Song, et al., Org. Electron. 48 (2017) 61-67. doi: 10.1016/j.orgel.2017.05.012
34. [34]
  I. Jeon, S. Zeljkovic, K. Kondo, et al., ACS Appl. Mater. Interfaces 8 (2016) 29866-29871. doi: 10.1021/acsami.6b09684
35. [35]
  S. Liao, H. Jhuo, Y. Cheng, et al., J. Mater. Chem. A 3 (2015) 22599-22604. doi: 10.1039/C5TA05216E
36. [36]
  Z. Zhang, H. Li, B. Qi, et al., J. Mater. Chem. A 1 (2013) 9624. doi: 10.1039/c3ta12478a
37. [37]
  X. Han, Z. Li, Z. Ding, et al., Nano Res. 11 (2018) 4293-4301. doi: 10.1007/s12274-018-2015-y
38. [38]
  Y. Wang, X. Li, L. Zhu, et al., Adv. Energy Mater. 7 (2017) 1701144.
39. [39]
  C. Sun, Z. Wu, H. Yip, et al., Adv. Energy Mater. 6 (2016) 1501534.
40. [40]
  J. Wang, K. Lin, K. Zhang, et al., Adv. Energy Mater. 6 (2016) 1502563.
41. [41]
  J. Liu, J. Li, X. Liu, et al., Macromol. Chem. Phys. (2019) 1800477.
42. [42]
  C. Cui, Y. Li, Y. Li, et al., Adv. Energy Mater. 7 (2017) 1601251.
43. [43]
  C. Duan, K. Zhang, C. Zhong, et al., Chem. Soc. Rev. 42 (2013) 9071-9104. doi: 10.1039/c3cs60200a
44. [44]
  L. Derue, O. Dautel, A. Tournebize, et al., Adv. Mater. 26 (2014) 5831-5838. doi: 10.1002/adma.201401062
45. [45]
  J. Liu, J. Li, G. Tu, Front. Optoelectron. 11 (2019) 348-359.
46. [46]
  T. Nguyen, T. Lee, B. Gautam, et al., Adv. Funct. Mater. 27 (2017) 1702474. doi: 10.1002/adfm.201702474
47. [47]
  J. Liu, J. Li, X. Liu, et al., ACS Appl. Mater. Interfaces 10 (2018) 2649-2657. doi: 10.1021/acsami.7b18331
48. [48]
  J. Liu, C. Gao, X. He, et al., ACS Appl. Mater. Interfaces 7 (2015) 24008-24015. doi: 10.1021/acsami.5b06780
49. [49]
  S. Xie, J. Wang, R. Wang, et al., Chin. Chem. Lett. 30 (2019) 217-221. doi: 10.1016/j.cclet.2018.04.001
50. [50]
  Z. Wen, X. Ma, X. Yang, et al., Chin. Chem. Lett. 30 (2019) 995-999. doi: 10.1016/j.cclet.2019.01.028
51. [51]
  Y. Shi, C. Yang, H. Li, et al., Chin. Chem. Lett. 30 (2019) 906-910. doi: 10.1016/j.cclet.2019.01.031
52. [52]
  J. Seo, R. Yang, J. Brzezinski, et al., Adv. Mater. 21 (2009) 1006-1011. doi: 10.1002/adma.200802420
53. [53]
  J. Kong, I. Hwang, K. Lee, Adv. Mater. 26 (2014) 6275-6283. doi: 10.1002/adma.201402182
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