Citation: FENG Shiyu, LU Hao, LIU Zekun, LIU Yahui, LI Cuihong, BO Zhishan. Designing a High-Performance A-D-A Fused-Ring Electron Acceptor via Noncovalently Conformational Locking and Tailoring Its End Groups[J]. Acta Physico-Chimica Sinica, ;2019, 35(4): 355-360. doi: 10.3866/PKU.WHXB201805161 shu

Designing a High-Performance A-D-A Fused-Ring Electron Acceptor via Noncovalently Conformational Locking and Tailoring Its End Groups

Beijing Key Laboratory of Energy Conversion and Storage Materials, College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China

Corresponding author: LI Cuihong, licuihong@bnu.edu.cn BO Zhishan, zsbo@bnu.edu.cn
Received Date: 23 April 2018
Revised Date: 11 May 2018
Accepted Date: 11 May 2018
Available Online: 16 April 2018
Fund Project: the Beijing Natural Science Foundation, China 2182030The project was supported by the National Natural Science Foundation of China (21574013) and the Beijing Natural Science Foundation, China (2182030)the National Natural Science Foundation of China 21574013

Recently, non-fullerene polymer solar cells (NPSCs) have been developed rapidly because of the flexible energy-level variability and excellent optical absorption properties of non-fullerene electron acceptors. Among them, fused-ring electron acceptors (FREAs) with acceptor-donor- acceptor (A-D-A) structures have been extensively exploited in high-performance NPSCs. These FREAs often employ central aromatic fused rings attached to several rigid side-chains and flanked by two electron-deficient terminals. Many efforts have focused on the modification of the central flat conjugated backbone in order to gain broad and strong absorption and dense stacking. However, the preparation of such FREAs is relatively complex, especially for large fused-ring structures. In a previous work, we provided a simple and useful method to extend the effective conjugation length and broaden the absorption spectrum of the acceptor by noncovalent intramolecular interactions. On this basis, in this work, we have designed and synthesized a new A-D-A-type FREA (ITOIC-2Cl) that uses 4, 9-dihydro-s-indaceno[1, 2-b:5, 6-b']dithiophene (IDT) as a central donor unit, bis(alkoxy)-substituted thiophene rings as conformational locking π-bridges between the donor and acceptor units, and cyanoindanones modified with two high-electron-affinity chlorine atoms as end-capping acceptor units. On one hand, we can attain good backbone planarity in the solid state via the noncovalent conformational locking induced by sulfur−oxygen (S···O) and oxygen−hydrogen (CH···O) interactions, which are not strong enough to lock the coplanar conformation in solution, thus simultaneously endowing ITOIC-2Cl with good solubility. On the other hand, we can enhance the intramolecular charge transfer by enhancing the electron deficiency of the terminal groups. The optical and electrochemical properties of ITOIC-2Cl were systematically explored. Moreover, in combination with the donor polymer of [(2, 6-(4, 8-bis(5-(2-ethylhexyl)thiophen-2-yl)-benzo[1, 2-b:4, 5-b']dithiophene))-alt-(5, 5-(1', 3'-di-2-thienyl-5', 7'-bis(2-ethylhexyl)benzo[1', 2'-c:4', 5'-c']dithiophene-4, 8-dione))] (PBDB-T), the photovoltaic performances of the devices and the corresponding blend morphologies were studied. ITOIC-2Cl exhibited a broad absorption spectrum up to 900 nm, which is beneficial for broad harvesting of photons across the visible and NIR region. The PBDB-T:ITOIC-2Cl-based blend films exhibited favorable fibrous nanostructures with appropriate nanoscale phase separation, verified by atomic force microscopy and transmission electron microscopy characterizations. This morphology is beneficial for charge transport. Through the space-charge-limited current measurement, the PBDB-T:ITOIC-2Cl-based device exhibited the high hole/electron mobility of 1.85 × 10⁻⁴/1.19 × 10⁻⁴ cm²∙V⁻¹∙s⁻¹. The PBDB-T:ITOIC-2Cl-based devices obtained a high power conversion efficiency of 9.37%, with an open-circuit voltage (V_oc) of 0.886 V, short-circuit current (J_sc) of 17.09 mA cm⁻², and a fill factor (FF) of 61.8%. These results thus demonstrate the efficacy of the proposed strategy for designing high-performance non-fullerene FREAs.
- Non-fullerene,
- Polymer solar cell,
- Fused-ring electron acceptor,
- Conformational locking,
- Intramolecular charge transfer
1. [1]
  Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270(5243), 1789. doi: 10.1126/science.270.5243.1789 doi: 10.1126/science.270.5243.1789
2. [2]
  Lu, L. Y.; Zheng, T. Y.; Wu, Q. H.; Schneider, A. M.; Zhao, D. L.; Yu, L. P. Chem. Rev. 2015, 115(23), 12666. doi: 10.1021/acs.chemrev.5b00098 doi: 10.1021/acs.chemrev.5b00098
3. [3]
  Li, Y. F. Acc. Chem. Res. 2012, 45(5), 723. doi: 10.1021/ar2002446 doi: 10.1021/ar2002446
4. [4]
  Krebs, F. C. Sol. Energy Mater. Sol. Cells 2009, 93(4), 393. doi: 10.1016/j.solmat.2008.12.008 doi: 10.1016/j.solmat.2008.12.008
5. [5]
  Zhao, Y.F.; Zou, W.J.; Li, H.; Lu, K.; Yan, W.; Wei, Z. X. Chin. J. Polym. Sci. 2017, 35(2), 261. doi: 10.1007/s10118-017-1875-z doi: 10.1007/s10118-017-1875-z
6. [6]
  Gelinas, S.; Rao, A.; Kumar, A.; Smith, S. L.; Chin, A. W.; Clark, J.; van der Poll, T. S.; Bazan, G. C.; Friend, R. H. Science2014, 343(6170), 512. doi:10.1126/science.1246249 doi: 10.1126/science.1246249
7. [7]
  Zhao, J. B.; Li, Y. K.; Yang, G. F.; Jiang, K.; Lin, H. R.; Ade, H.; Ma, W.; Yan, H. Nat. Energy 2016, 1, 15027. doi: 10.1038/nenergy.2015.27 doi: 10.1038/nenergy.2015.27
8. [8]
  Lin, Y. Z.; Zhang, Z. G.; Bai, H. T.; Wang, J. Y.; Yao, Y. H.; Li, Y. F.; Zhu, D. B.; Zhan, X. W. Energy Environ. Sci. 2015, 8(2), 610. doi: 10.1039/c4ee03424d doi: 10.1039/c4ee03424d
9. [9]
  Lin, Y. Z.; Wang, J. Y.; Zhang, Z. G.; Bai, H. T.; Li, Y. F.; Zhu, D. B.; Zhan, X. W. Adv. Mater. 2015, 27(7), 1170. doi: 10.1002/adma.201404317 doi: 10.1002/adma.201404317
10. [10]
  Fan, Q. P.; Su, W. Y.; Wang, Y.; Guo, B.; Jiang, Y. F.; Guo, X.; Liu, F.; Russell, T. P.; Zhang, M. J.; Li, Y. F. Sci. China Chem. 2018, 61, 531. doi: 10.1007/s11426-017-9199-1 doi: 10.1007/s11426-017-9199-1
11. [11]
  Zhao, W. C.; Li, S. S.; Yao, H. F.; Zhang, S. Q.; Zhang, Y.; Yang, B.; Hou, J. H. J. Am. Chem. Soc. 2017, 139(21), 7148. doi: 10.1021/jacs.7b02677 doi: 10.1021/jacs.7b02677
12. [12]
  Zhang, S.; Qin, Y.; Zhu, J.; Hou, J. Adv. Mater. 2018. doi: 10.1002/adma.201800868 doi: 10.1002/adma.201800868
13. [13]
  Liu, Y. H.; Zhang, Z.; Feng, S. Y.; Li, M.; Wu, L. L.; Hou, R.; Xu, X. J.; Chen, X. B.; Bo, Z. S. J. Am. Chem. Soc. 2017, 139(9), 3356. doi: 10.1021/jacs.7b00566 doi: 10.1021/jacs.7b00566
14. [14]
  Hou, J. H.; Inganas, O.; Friend, R. H.; Gao, F. Nat. Mater. 2018, 17(2), 119. doi: 10.1038/nmat5063 doi: 10.1038/nmat5063
15. [15]
  Zhang, G.; Zhao, J.; Chow, P. C. Y.; Jiang, K.; Zhang, J.; Zhu, Z.; Zhang, J.; Huang, F.; Yan, H. Chem. Rev. 2018. doi: 10.1021/acs.chemrev.7b00535 doi: 10.1021/acs.chemrev.7b00535
16. [16]
  Yan, C.; Barlow, S.; Wang, Z.; Yan, H.; Jen, A. K. Y.; Marder, S. R.; Zhan, X. Nat. Rev. Mater. 2018, 3, 18003. doi: 10.1038/natrevmats.2018.3 doi: 10.1038/natrevmats.2018.3
17. [17]
  Yang, Y.; Jiang, X.; Zhan, X. W.; Chen, X. G. Acta Phys. -Chim. Sin. 2019, 35, 257. doi: 10.3866/PKU.WHXB201803191
18. [18]
  Feng, S. Y.; Ma, D. Y.; Wu, L. L.; Liu, Y. H.; Zhang, C. E.; Xu, X. J.; Chen, X. B.; Yan, S. K.; Bo, Z. S. Sci. China Chem. 2018, doi: 10.1007/s11426-018-9252-9 doi: 10.1007/s11426-018-9252-9
19. [19]
  Yao, H. F.; Chen, Y.; Qin, Y. P.; Yu, R. N.; Cui, Y.; Yang, B.; Li, S. S.; Zhang, K.; Hou, J. H. Adv. Mater. 2016, 28(37), 8283. doi: 10.1002/adma.201602642 doi: 10.1002/adma.201602642
20. [20]
  Tang, M. L.; Oh, J. H.; Reichardt, A. D.; Bao, Z. N. J. Am. Chem. Soc. 2009, 131(10), 3733. doi: 10.1021/ja809045s doi: 10.1021/ja809045s
21. [21]
  Li, Y. X.; Lin, J. D.; Che, X. Z.; Qu, Y.; Liu, F.; Liao, L. S.; Forrest, S. R. J. Am. Chem. Soc. 2017, 139(47), 17114. doi: 10.1021/jacs.7b11278 doi: 10.1021/jacs.7b11278
22. [22]
  Cui, Y.; Yang, C. Y.; Yao, H. F.; Zhu, J.; Wang, Y. M.; Jia, G. X.; Gao, F.; Hou, J. H. Adv. Mater. 2017, 29(43). doi: 10.1002/adma.201703080 doi: 10.1002/adma.201703080
23. [23]
  Zhang, C.; Nguyen, T. H.; Sun, J. Y.; Li, R.; Black, S.; Bonner, C. E.; Sun, S. S. Macromolecules 2009, 42(3), 663. doi: 10.1021/ma802621b doi: 10.1021/ma802621b
24. [24]
  Yao, H. F.; Cui, Y.; Yu, R. N.; Gao, B. W.; Zhang, H.; Hou, J. H. Angew. Chem. Int. Ed. 2017, 56(11), 3045. doi: 10.1002/anie.201610944 doi: 10.1002/anie.201610944
25. [25]
  Xu, X. P.; Zhang, G. J.; Zhao, Y. Z.; Liu, J.; Li, Y.; Peng, Q. Chin. J. Polym. Sci. 2017, 35(2), 249.
26. [26]
  Li, Y. X.; Qian, D. P.; Zhong, L.; Lin, J. D.; Jiang, Z. Q.; Zhang, Z. G.; Zhang, Z. J.; Li, Y. F.; Liao, L. S.; Zhang, F. L. Nano Energy 2016, 27, 430. doi: 10.1016/j.nanoen.2016.07.019 doi: 10.1016/j.nanoen.2016.07.019
27. [27]
  Feng, S. Y.; Hou, R.; Xu, Q.; Liu, Y. H.; Zhang, J. Q.; Gong, X.; Li, C. H.; Lu, K.; Wei, Z. X.; Bo, Z. S. Sol. Energy Mater. Sol. Cells 2016, 154, 42. doi: 10.1016/j.solmat.2016.04.026 doi: 10.1016/j.solmat.2016.04.026
28. [28]
  Yuan, J.; Hua, Y.; Zhu, C.; Shen, P.; Wan, M. X.; Feng, L. L.; Zou, Y. P. Acta Phys. -Chim. Sin. 2018, 34, 1272. doi: 10.3866/PKU.WHXB201803221
29. [29]
  Feng, S. Y.; Zhang, C. E.; Liu, Y. H.; Bi, Z. Z.; Zhang, Z.; Xu, X. J.; Ma, W.; Bo, Z. S. Adv. Mater. 2017, 29(42). doi: 10.1002/adma.201703527 doi: 10.1002/adma.201703527
30. [30]
  Zhang, C. E.; Feng, S. Y.; Liu, Y. H.; Hou, R.; Zhang, Z.; Xu, X. J.; Wu, Y. Z.; Bo, Z. S. ACS Appl. Mater. Interfaces 2017, 9(39), 33906. doi: 10.1021/acsami.7b09915 doi: 10.1021/acsami.7b09915
31. [31]
  Li, W. W.; Hendriks, K. H.; Furlan, A.; Roelofs, W. S. C.; Wienk, M. M.; Janssen, R. A. J. J. Am. Chem. Soc. 2013, 135(50), 18942. doi: 10.1021/ja4101003 doi: 10.1021/ja4101003
32. [32]
  Jia, G. X.; Zhang, S. Q.; Yang, L. Y.; He, C.; Fan, H. L.; Hou, J. H. Acta Phys. -Chim. Sin. 2019, 35, 76. doi: 10.3866/PKU.WHXB201712063
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