Citation: Wenxiang Ma, Xinyu He, Tianyi Chen, De-Li Ma, Hongzheng Chen, Chang-Zhi Li. Near-infrared non-fused electron acceptors for efficient organic photovoltaics[J]. Chinese Chemical Letters, ;2024, 35(4): 109099. doi: 10.1016/j.cclet.2023.109099 shu

Near-infrared non-fused electron acceptors for efficient organic photovoltaics

State Key Laboratory of Silicon and Advanced Semiconductor Materials, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China

czli@zju.edu.cn

Received Date: 18 July 2023
Revised Date: 11 September 2023
Accepted Date: 13 September 2023
Available Online: 15 September 2023

Figures(5)

Developing narrow-bandgap organic semiconductors is important to facilitate the advancement of organic photovoltaics (OPVs). Herein, two near-infrared non-fused ring acceptors (NIR NFRAs), PTBFTT-F and PTBFTT-Cl have been developed with A-π_A-π_D-D-π_D-π_A-A non-fused structures. It is revealed that the introduction of electron deficient π-bridge (π_A) and multiple intramolecular noncovalent interactions effectively retained the structural planarity and intramolecular charge transfer of NFRAs, extending strong NIR photon absorption up to 950 nm. Further, the chlorinated acceptor, with the enlarged π-surface compared to the fluorinated counterpart, promoted not only molecular stacking in solid, but also the desirable photochemical stability in ambient, which are helpful to thereby improve the exciton and charge dynamics for the corresponding OPVs. Overall, this work provides valuable insights into the design of NIR organic semiconductors.
- Organic photovoltaic,
- Near-infrared,
- Non-fused electron acceptor,
- Noncovalent interaction,
- Stability
1. [1]
  A. Armin, W. Li, O.J. Sandberg, et al., Adv. Energy Mater. 11 (2021) 2003570. doi: 10.1002/aenm.202003570
2. [2]
  Y. Liu, B. Liu, C.Q. Ma, et al., Sci. China Chem. 65 (2022) 224–268. doi: 10.1007/s11426-021-1180-6
3. [3]
  S. Karuthedath, J. Gorenflot, Y. Firdaus, et al., Nat. Mater. 20 (2021) 378–384. doi: 10.1038/s41563-020-00835-x
4. [4]
  Q. Shen, C. He, S. Li, et al., Acc. Mater. Res. 3 (2022) 644–657. doi: 10.1021/accountsmr.2c00052
5. [5]
  Q.Q. Zhang, C.Z. Li, Chem. Eng. J. 452 (2023) 139312. doi: 10.1016/j.cej.2022.139312
6. [6]
  J. Yuan, Y. Zhang, L. Zhou, et al., Joule 3 (2019) 1140–1151. doi: 10.1016/j.joule.2019.01.004
7. [7]
  L. Zhu, M. Zhang, J. Xu, et al., Nat. Mater. 21 (2022) 656–663. doi: 10.1038/s41563-022-01244-y
8. [8]
  J. Gao, N. Yu, Z. Chen, et al., Adv. Sci. 9 (2022) 2203606. doi: 10.1002/advs.202203606
9. [9]
  L. Zhan, S. Li, Y. Li, et al., Adv. Energy Mater. 12 (2022) 2201076. doi: 10.1002/aenm.202201076
10. [10]
  T. Chen, S. Li, Y. Li, et al., Adv. Mater. 35 (2023) 2300400. doi: 10.1002/adma.202300400
11. [11]
  X. Xu, W. Jing, H. Meng, et al., Adv. Mater. 35 (2023) 2208997. doi: 10.1002/adma.202208997
12. [12]
  C.J. Traverse, R. Pandey, M.C. Barr, R.R. Lunt, Nat. Energy 2 (2017) 849–860. doi: 10.1038/s41560-017-0016-9
13. [13]
  D. Wang, H. Liu, Y. Li, et al., Joule 5 (2021) 945–957. doi: 10.1016/j.joule.2021.02.010
14. [14]
  D. Wang, Y. Li, G. Zhou, et al., Energy Environ. Sci. 15 (2022) 2629–2637. doi: 10.1039/D2EE00977C
15. [15]
  J. Ren, X. Shu, Y. Wang, et al., Chin. Chem. Lett. 33 (2022) 1650–1658. doi: 10.1016/j.cclet.2021.10.052
16. [16]
  X. Li, R. Xia, K. Yan, et al., ACS Energy Lett. 5 (2020) 3115–3123. doi: 10.1021/acsenergylett.0c01554
17. [17]
  Y. Li, C. He, L. Zuo, et al., Adv. Energy Mater. 11 (2021) 2003408. doi: 10.1002/aenm.202003408
18. [18]
  H. Yao, Y. Chen, Y. Qin, et al., Adv. Mater. 28 (2016) 8283–8287. doi: 10.1002/adma.201602642
19. [19]
  H. Yao, Y. Cui, R. Yu, et al., Angew. Chem. Int. Ed. 56 (2017) 3045–3049. doi: 10.1002/anie.201610944
20. [20]
  F.X. Chen, J.Q. Xu, Z.X. Liu, et al., Adv. Mater. 30 (2018) 1803769. doi: 10.1002/adma.201803769
21. [21]
  Z. Xiao, X. Jia, D. Li, et al., Sci. Bull. 62 (2017) 1494–1496. doi: 10.1016/j.scib.2017.10.017
22. [22]
  Z. Jia, S. Qin, L. Meng, et al., Nat. Commun. 12 (2021) 178. doi: 10.1038/s41467-020-20431-6
23. [23]
  W. Liu, S. Sun, S. Xu, et al., Adv. Mater. 34 (2022) 2200337. doi: 10.1002/adma.202200337
24. [24]
  J. Li, H. Li, L. Ma, S. Zhang, J. Hou, Chin. J. Chem. 41 (2023) 424–430. doi: 10.1002/cjoc.202200579
25. [25]
  H. Li, J. Li, C. Yang, et al., J. Mater. Chem. C 11 (2023) 6155–6161. doi: 10.1039/D3TC00625E
26. [26]
  Z. Jia, Q. Ma, Z. Chen, et al., Nat. Commun. 14 (2023) 1236. doi: 10.1038/s41467-023-36917-y
27. [27]
  T. Li, S. Dai, Z. Ke, et al., Adv. Mater. 30 (2018) 1705969. doi: 10.1002/adma.201705969
28. [28]
  Z. Yao, X. Liao, K. Gao, et al., J. Am. Chem. Soc. 140 (2018) 2054–2057. doi: 10.1021/jacs.7b13239
29. [29]
  Y. Li, X. Liu, F.P. Wu, et al., J. Mater. Chem. A 4 (2016) 5890–5897. doi: 10.1039/C6TA00612D
30. [30]
  S. Liu, J. Yuan, W. Deng, et al., Nat. Photonics 14 (2020) 300–305.
31. [31]
  C. He, Y. Li, Y. Liu, et al., J. Mater. Chem. A 8 (2020) 18154–18161. doi: 10.1039/D0TA06907H
32. [32]
  Y. Zhou, M. Li, H. Lu, et al., Adv. Funct. Mater. 31 (2021) 2101742. doi: 10.1002/adfm.202101742
33. [33]
  X. Wang, R. Zeng, H. Lu, et al., Chin. J. Chem. 41 (2023) 665–671. doi: 10.1002/cjoc.202200673
34. [34]
  Y. Liu, Z. Zhang, S. Feng, et al., J. Am. Chem. Soc. 139 (2017) 3356–3359. doi: 10.1021/jacs.7b00566
35. [35]
  S. Li, L. Zhan, F. Liu, et al., Adv. Mater. 30 (2018) 1705208. doi: 10.1002/adma.201705208
36. [36]
  Z. Zhang, S. Zhang, Z. Liu, et al., Acta Phys. Chim. Sin. 35 (2019) 394–400. doi: 10.3866/PKU.WHXB201805091
37. [37]
  Z.P. Yu, Z.X. Liu, F.X. Chen, et al., Nat. Commun. 10 (2019) 2152. doi: 10.1038/s41467-019-10098-z
38. [38]
  H. Huang, Q. Guo, S. Feng, et al., Nat. Commun. 10 (2019) 3038. doi: 10.1038/s41467-019-11001-6
39. [39]
  T.J. Wen, Z.X. Liu, Z. Chen, et al., Angew. Chem. Int. Ed. 60 (2021) 12964–12970. doi: 10.1002/anie.202101867
40. [40]
  L. Ma, S. Zhang, J. Zhu, et al., Nat. Commun. 12 (2021) 5093. doi: 10.1038/s41467-021-25394-w
41. [41]
  M. Yang, W. Wei, X. Zhou, Z. Wang, C. Duan, Energy Mater. 1 (2021) 100008.
42. [42]
  S.Y. Liu, D. Wang, T.J. Wen, et al., Chin. J. Polym. Sci. 40 (2022) 944–950. doi: 10.1007/s10118-022-2750-0
43. [43]
  T.J. Wen, J. Xiang, N. Jain, et al., J. Energy Chem. 70 (2022) 576–582. doi: 10.1016/j.jechem.2022.03.030
44. [44]
  R. Hou, M. Li, X. Ma, et al., ACS Appl. Mater. Interfaces 12 (2020) 46220–46230. doi: 10.1021/acsami.0c13993
45. [45]
  X. Zhang, L. Qin, J. Yu, et al., Angew. Chem. Int. Ed. 60 (2021) 12475–12481. doi: 10.1002/anie.202100390
46. [46]
  Q. Shen, C. He, B. Wu, et al., Chem. Eng. J. 471 (2023) 144472. doi: 10.1016/j.cej.2023.144472
47. [47]
  D.L. Ma, Q.Q. Zhang, C.Z. Li, Angew. Chem. Int. Ed. 62 (2023) e202214931. doi: 10.1002/anie.202214931
48. [48]
  L. Ma, S. Zhang, J. Ren, et al., Angew. Chem. Int. Ed. 62 (2022) e202214088.
49. [49]
  Y. Shao, R. Sun, W. Wang, et al., Sci. China Chem. 66 (2023) 1101–1110. doi: 10.1007/s11426-022-1502-3
50. [50]
  C. Li, X. Zhang, N. Yu, et al., Adv. Funct. Mater. 32 (2021) 2108861.
51. [51]
  C. He, Y. Li, S. Li, et al., ACS Appl. Mater. Interfaces 12 (2020) 16700–16706. doi: 10.1021/acsami.0c00837
52. [52]
  T.J. Wen, D. Wang, L. Tao, et al., ACS Appl. Mater. Interfaces 12 (2020) 39515–39523. doi: 10.1021/acsami.0c12100
53. [53]
  Q. Wen, Q. Cai, P. Fu, et al., Chin. Chem. Lett. 34 (2023) 107592. doi: 10.1016/j.cclet.2022.06.015
54. [54]
  Y. Sakamoto, S. Komatsu, T. Suzuki, J. Am. Chem. Soc. 123 (2001) 4643–4644. doi: 10.1021/ja015712j
55. [55]
  S. Feng, M. Li, N. Tang, et al., ACS Appl. Mater. Interfaces 12 (2020) 4638–4648. doi: 10.1021/acsami.9b18076
56. [56]
  Z.X. Liu, Z.P. Yu, Z. Shen, et al., Nat. Commun. 12 (2021) 3049. doi: 10.1038/s41467-021-23389-1
57. [57]
  X. Zhang, C. Li, L. Qin, et al., Angew. Chem. Int. Ed. 60 (2021) 17720–17725. doi: 10.1002/anie.202106753
58. [58]
  X. Zhang, G. Li, S. Mukherjee, et al., Adv. Energy Mater. 12 (2021) 2102172.
1. [1]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
2. [2]
  Yupeng Liu , Hui Wang , Songnan Qu . Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application. Chinese Chemical Letters, 2025, 36(5): 110618-. doi: 10.1016/j.cclet.2024.110618
3. [3]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
4. [4]
  Dandan Tang , Ningge Xu , Yuyang Fu , Wei Peng , Jinsheng Wu , Heng Liu , Fabiao Yu . Rationally designed an innovative proximity labeling near-infrared fluorogenic probe for imaging of peroxynitrite in acute lung injury. Chinese Chemical Letters, 2025, 36(5): 110082-. doi: 10.1016/j.cclet.2024.110082
5. [5]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
6. [6]
  Keliang Li , Guoqiang Dong , Shanchao Wu , Chunquan Sheng . Discovery of an activatable near-infrared fluorescent and theranostic PROTAC for tumor-targeted detecting and degrading of BRD4. Chinese Chemical Letters, 2025, 36(6): 110280-. doi: 10.1016/j.cclet.2024.110280
7. [7]
  Xianzhu Luo , Feifei Yu , Rui Wang , Tian Su , Pan Luo , Pengfei Wen , Fabiao Yu . A near-infrared two-photon fluorescent probe for the detection of HClO in inflammatory and tumor-bearing mice. Chinese Chemical Letters, 2025, 36(7): 110531-. doi: 10.1016/j.cclet.2024.110531
8. [8]
  Xu Qu , Baohua Ji , Haocheng Gong , Guangwei Wang , Liang-Liang Gao , Jing Zhang , Jianjian Zhang , Yuan Guo . Dual-emissive near-infrared fluorogenic probe with enhanced cellular uptake capability for sensitive tracking of cellular polarity. Chinese Chemical Letters, 2025, 36(10): 110766-. doi: 10.1016/j.cclet.2024.110766
9. [9]
  Wenping Dong , Mo Ma , Jingkang Li , Lanlan Xu , Dejiang Gao , Pinyi Ma , Daqian Song . Near-infrared fluorescent probe with large Stokes shift and long emission wavelength for rapid diagnosis of lung cancer via aerosol inhalation delivery. Chinese Chemical Letters, 2025, 36(5): 110147-. doi: 10.1016/j.cclet.2024.110147
10. [10]
  Rongjun Zhao , Tai Wu , Yong Hua , Yude Wang . Improving performance of perovskite solar cells enabled by defects passivation and carrier transport dynamics regulation via organic additive. Chinese Chemical Letters, 2025, 36(2): 109587-. doi: 10.1016/j.cclet.2024.109587
11. [11]
  Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
12. [12]
  Qiyan Wu , Ruixin Zhou , Zhangyi Yao , Tanyuan Wang , Qing Li . Effective approaches for enhancing the stability of ruthenium-based electrocatalysts towards acidic oxygen evolution reaction. Chinese Chemical Letters, 2024, 35(10): 109416-. doi: 10.1016/j.cclet.2023.109416
13. [13]
  Xingang Kong , Yabei Su , Cuijuan Xing , Weijie Cheng , Jianfeng Huang , Lifeng Zhang , Haibo Ouyang , Qi Feng . Facile synthesis of porous TiO₂/SnO₂ nanocomposite as lithium ion battery anode with enhanced cycling stability via nanoconfinement effect. Chinese Chemical Letters, 2024, 35(11): 109428-. doi: 10.1016/j.cclet.2023.109428
14. [14]
  Xinpin Pan , Yongjian Cui , Zhe Wang , Bowen Li , Hailong Wang , Jian Hao , Feng Li , Jing Li . Robust chemo-mechanical stability of additives-free SiO₂ anode realized by honeycomb nanolattice for high performance Li-ion batteries. Chinese Chemical Letters, 2024, 35(10): 109567-. doi: 10.1016/j.cclet.2024.109567
15. [15]
  Ziling Jiang , Chen Liu , Jie Yang , Xia Li , Chaochao Wei , Qiyue Luo , Zhongkai Wu , Lin Li , Liping Li , Shijie Cheng , Chuang Yu . Designing F-doped Li₃InCl₆ electrolyte with enhanced stability for all-solid-state lithium batteries in a wide voltage window. Chinese Chemical Letters, 2025, 36(6): 109741-. doi: 10.1016/j.cclet.2024.109741
16. [16]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
17. [17]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
18. [18]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
19. [19]
  Shupeng Han , Caiting Deng , Meichen Zheng , Linwei Yang , Hancun Kong , Yongchao He , Yinuo Zheng , Guowei Deng , Yu Ren , Feifei An . A GSH-responsive NIR-BODIPY fluorophore with large Stokes-shift for tumor specific fluorescence imaging and surgical guidance. Chinese Chemical Letters, 2025, 36(7): 110459-. doi: 10.1016/j.cclet.2024.110459
20. [20]
  Zhouze Chen , Yujie Yan , Jun Luo , Pengnian Shan , Changyu Lu , Feng Guo , Weilong Shi . Piezoelectric effect synergistically boosted NIR-driven photothermal-assisted photocatalytic hydrogen evolution. Chinese Chemical Letters, 2025, 36(10): 111302-. doi: 10.1016/j.cclet.2025.111302

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(888)
HTML views(46)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142