Citation: Wenbin Lai, Safakath Karuthedath, Chengyi Xiao, Lei Meng, Frédéric Laquai, Weiwei Li, Yongfang Li. Alkyl-thiophene-alkyl linkers to construct double-cable conjugated polymers for single-component organic solar cells[J]. Chinese Chemical Letters, ;2024, 35(1): 108287. doi: 10.1016/j.cclet.2023.108287 shu

Alkyl-thiophene-alkyl linkers to construct double-cable conjugated polymers for single-component organic solar cells

Wenbin Lai ^{a, d, 1} ,
Safakath Karuthedath ^{c, e, 1} ,
Chengyi Xiao ^{b, *,} ,
Lei Meng ^{a, d} ,
Frédéric Laquai ^c ,
Weiwei Li ^{b, *,} ,
Yongfang Li ^{a, d}

a.
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
Beijing Advanced Innovation Center for Soft Matter Science and Engineering & State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China
c.
King Abdullah University of Science and Technology (KAUST), KAUST Solar Center (KSC), Physical Sciences and Engineering Division (PSE), Material Science and Engineering Program (MSE), Thuwal 23955-6900, Kingdom of Saudi Arabia
d.
University of Chinese Academy of Sciences, Beijing 100049, China
e.
Institute of Materials Research, Tsinghua Shenzhen International Graduate School, Tsinghua University, Shenzhen 518055, China

xiaocy@mail.buct.edu.cn

liweiwei@iccas.ac.cn

Received Date: 17 January 2023
Revised Date: 8 February 2023
Accepted Date: 1 March 2023
Available Online: 5 March 2023

Figures(6)

In this work, semirigid linkers of the alkyl-thiophene-alkyl structure are developed to construct double-cable polymers. Three alkyl units, propyl (C₃H₆), hexyl (C₆H₁₂), and dodecyl (C₁₂H₂₄), are applied as semirigid linkers, yielding three double-cable polymers: PBC6-T, PBC12-T, and PBC24-T, respectively. PBC12-T which uses C₆H₁₂-thiophene-C₆H₁₂ linkers is found to exhibit the best device efficiency of 5.56%, while PBC6-T and PBC24-T with shorter or longer linkers yield device efficiencies of only 2.65% and 1.09% in single-component organic solar cells (SCOSCs). Further studies reveal that PBC12-T exhibits higher crystallinity and improved charge transport, resulting in better efficiencies. Our work provides an approach to construct double-cable conjugated polymers with long alkyl linkers, and it shows the importance of the linker length for the photovoltaic performance of SCOSCs.
- Double-cable conjugated polymer,
- Single-component organic solar cellCrystallinity,
- Semirigid linkers,
- Alkyl-thiophene-alkyl
1. [1]
  Y. Lin, J. Wang, Z.G. Zhang, et al., Adv. Mater. 27 (2015) 1170–1174. doi: 10.1002/adma.201404317
2. [2]
  J. Yuan, Y. Zhang, L. Zhou, et al., Joule 3 (2019) 1140–1151. doi: 10.1016/j.joule.2019.01.004
3. [3]
  S. Chen, D. Meng, J. Huang, et al., CCS Chem. 3 (2021) 78–84. doi: 10.31635/ccschem.021.202000538
4. [4]
  L. Zhu, M. Zhang, J. Xu, et al., Nat. Mater. 21 (2022) 656–663. doi: 10.1038/s41563-022-01244-y
5. [5]
  Y. Cui, Y. Xu, H. Yao, et al., Adv. Mater. 33 (2021) e2102420. doi: 10.1002/adma.202102420
6. [6]
  L. Zhan, S. Li, Y. Li, et al., Joule 6 (2022) 662–675. doi: 10.1016/j.joule.2022.02.001
7. [7]
  X. Kong, J. Zhang, L. Meng, et al., CCS Chem. (2022) 1–10.
8. [8]
  Y.H. Liu, B.W. Liu, C.Q. Ma, et al., Sci. China Chem. 65 (2022) 1457–1497. doi: 10.1007/s11426-022-1256-8
9. [9]
  S. Park, T. Kim, S. Yoon, et al., Adv. Mater. 32 (2020) e2002217. doi: 10.1002/adma.202002217
10. [10]
  L. Meng, J. You, Y. Yang, Nat. Commun. 9 (2018) 5265. doi: 10.1038/s41467-018-07255-1
11. [11]
  P. Cheng, X.W. Zhan, Chem. Soc. Rev. 45 (2016) 2544–2582. doi: 10.1039/C5CS00593K
12. [12]
  B. Walker, A.B. Tamayo, X.D. Dang, et al., Adv. Funct. Mater. 19 (2009) 3063–3069. doi: 10.1002/adfm.200900832
13. [13]
  Y. He, N. Li, T. Heumüller, et al., Joule 6 (2022) 1160–1171. doi: 10.1016/j.joule.2022.05.008
14. [14]
  Y.K. He, T. Heumuller, W.B. Lai, et al., Adv. Energy Mater. 9 (2019) 1900409. doi: 10.1002/aenm.201900409
15. [15]
  S. Liang, B. Liu, S. Karuthedath, et al., Angew. Chem. Int. Ed. 61 (2022) e202209316. doi: 10.1002/anie.202209316
16. [16]
  S. Liang, X. Jiang, C. Xiao, et al., Acc. Chem. Res. 54 (2021) 2227–2237. doi: 10.1021/acs.accounts.1c00070
17. [17]
  J. Roncali, I. Grosu, Adv. Sci. 6 (2019) 1801026. doi: 10.1002/advs.201801026
18. [18]
  J. Roncali, Adv. Energy Mater. 1 (2011) 147–160. doi: 10.1002/aenm.201000008
19. [19]
  D.D. Xia, C. Li, W.W. Li, Chem. Rec. 19 (2019) 962–972. doi: 10.1002/tcr.201800131
20. [20]
  Y. Liu, B. Liu, C.Q. Ma, et al., Sci. China Chem. 65 (2021) 224–268.
21. [21]
  C.H. Liu, C.Y. Xiao, C.C. Xie, W.W. Li, Nano Energy 89 (2021) 106399. doi: 10.1016/j.nanoen.2021.106399
22. [22]
  C. Xie, X. Jiang, Q. Zhu, et al., Small Methods 5 (2021) e2100481. doi: 10.1002/smtd.202100481
23. [23]
  C. Xie, C. Xiao, X. Jiang, et al., Macromolecules 55 (2021) 322–330. doi: 10.1007/s43032-020-00277-5
24. [24]
  Y. Wu, J. Guo, W. Wang, et al., Joule 5 (2021) 1800–1815. doi: 10.1016/j.joule.2021.05.002
25. [25]
  D. Wang, Z.F. Yang, F. Liu, et al., Chin. Chem. Lett. 33 (2022) 466–469. doi: 10.1016/j.cclet.2021.06.042
26. [26]
  A.M. Ramos, M.T. Rispens, J.K.J. van Duren, et al., J. Am. Chem. Soc. 123 (2001) 6714–6715. doi: 10.1021/ja015614y
27. [27]
  F. Zhang, M. Svensson, M.R. Andersson, et al., Adv. Mater. 13 (2001) 1871–1874. doi: 10.1002/1521-4095(200112)13:24<1871::AID-ADMA1871>3.0.CO;2-3
28. [28]
  Z.A. Tan, J. Hou, Y. He, et al., Macromolecules 40 (2007) 1868–1873. doi: 10.1021/ma070052+
29. [29]
  Y.H. Geng, Acta Phys. Chim. Sin. 35 (2019) 1311–1312. doi: 10.3866/PKU.WHXB201909019
30. [30]
  C. Li, X. Wu, X. Sui, et al., Angew. Chem. Int. Ed. 58 (2019) 15532–15540. doi: 10.1002/anie.201910489
31. [31]
  J. Song, Z. Bo, Chin. Chem. Lett. 34 (2023) 108163. doi: 10.1016/j.cclet.2023.108163
32. [32]
  J. Guo, Y. Wu, W. Wang, et al., Sol. RRL 6 (2022) 2101024. doi: 10.1002/solr.202101024
33. [33]
  J. Wang, X.D. Jiang, H.B. Wu, et al., Nat. Commun. 12 (2021) 6679. doi: 10.1038/s41467-021-26995-1
34. [34]
  G. Feng, W. Tan, S. Karuthedath, et al., Angew. Chem. Int. Ed. 60 (2021) 25499–25507. doi: 10.1002/anie.202111192
35. [35]
  Z.J. Hu, C.Y. Xiao, W.L. Tan, et al., Macromolecules 55 (2022) 5188–5196. doi: 10.1021/acs.macromol.2c00444
36. [36]
  G.T. Feng, J.Y. Li, Y.K. He, et al., Joule 3 (2019) 1765–1781. doi: 10.1016/j.joule.2019.05.008
37. [37]
  X. Jiang, J. Yang, S. Karuthedath, et al., Angew. Chem. Int. Ed. 59 (2020) 21683–21692. doi: 10.1002/anie.202009272
38. [38]
  F.C. Spano, Acc. Chem. Res. 43 (2010) 429–439. doi: 10.1021/ar900233v
39. [39]
  C. Wang, H. Dong, W. Hu, et al., Chem. Rev. 112 (2012) 2208–2267. doi: 10.1021/cr100380z
40. [40]
  C.Y. Xiao, C. Li, F. Liu, et al., J. Mater. Chem. C 8 (2020) 5370–5374. doi: 10.1039/D0TC00587H
41. [41]
  H. Sirringhaus, P.J. Brown, R.H. Friend, et al., Nature 401 (1999) 685–688. doi: 10.1038/44359
42. [42]
  C. Xiao, G. Zhao, A. Zhang, et al., Adv. Mater. 27 (2015) 4963–4968. doi: 10.1002/adma.201502617
43. [43]
  S. Karuthedath, A. Melianas, Z. Kan, et al., J. Mater. Chem. A 6 (2018) 7428–7438. doi: 10.1039/C8TA01692E
1. [1]
  Yikun Wang , Qiaomei Chen , Shijie Liang , Dongdong Xia , Chaowei Zhao , Christopher R. McNeill , Weiwei Li . Near-infrared double-cable conjugated polymers based on alkyl linkers with tunable length for single-component organic solar cells. Chinese Chemical Letters, 2024, 35(4): 109164-. doi: 10.1016/j.cclet.2023.109164
2. [2]
  Yuanzhe Lu , Yuanqin Zhu , Linfeng Zhong , Dingshan Yu . Long-lifespan aqueous alkaline and acidic batteries enabled by redox conjugated covalent organic polymer anodes. Chinese Journal of Structural Chemistry, 2024, 43(3): 100249-100249. doi: 10.1016/j.cjsc.2024.100249
3. [3]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
4. [4]
  Xin-Tong Zhao , Jin-Zhi Guo , Wen-Liang Li , Jing-Ping Zhang , Xing-Long Wu . Two-dimensional conjugated coordination polymer monolayer as anode material for lithium-ion batteries: A DFT study. Chinese Chemical Letters, 2024, 35(6): 108715-. doi: 10.1016/j.cclet.2023.108715
5. [5]
  Dong Lv , Xuelei Liu , Wei Li , Qiang Zhang , Xinhong Yu , Yanchun Han . Single droplet formation by controlling the viscoelasticity of polymer solutions during inkjet printing. Chinese Chemical Letters, 2024, 35(6): 109401-. doi: 10.1016/j.cclet.2023.109401
6. [6]
  Kunyao Peng , Xianbin Wang , Xingbin Yan . Converting LiNO₃ additive to single nitrogenous component Li₂N₂O₂ SEI layer on Li metal anode in carbonate-based electrolyte. Chinese Chemical Letters, 2024, 35(9): 109274-. doi: 10.1016/j.cclet.2023.109274
7. [7]
  Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376
8. [8]
  Zhiqiang Liu , Qiang Gao , Wei Shen , Meifeng Xu , Yunxin Li , Weilin Hou , Hai-Wei Shi , Yaozuo Yuan , Erwin Adams , Hian Kee Lee , Sheng Tang . Removal and fluorescence detection of antibiotics from wastewater by layered double oxides/metal-organic frameworks with different topological configurations. Chinese Chemical Letters, 2024, 35(8): 109338-. doi: 10.1016/j.cclet.2023.109338
9. [9]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
10. [10]
  Kangrong Yan , Ziqiu Shen , Yanchun Huang , Benfang Niu , Hongzheng Chen , Chang-Zhi Li . Curing the vulnerable heterointerface via organic-inorganic hybrid hole transporting bilayers for efficient inverted perovskite solar cells. Chinese Chemical Letters, 2024, 35(6): 109516-. doi: 10.1016/j.cclet.2024.109516
11. [11]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2023.100277
12. [12]
  Panke Zhou , Hong Yu , Mun Yin Chee , Tao Zeng , Tianli Jin , Hongling Yu , Shuo Wu , Wen Siang Lew , Xiong Chen . Electron push-pull effects induced performance promotion in covalent organic polymer thin films-based memristor for neuromorphic application. Chinese Chemical Letters, 2024, 35(5): 109279-. doi: 10.1016/j.cclet.2023.109279
13. [13]
  Jun Guo , Zhenbang Zhuang , Wanqiang Liu , Gang Huang . "Co-coordination force" assisted rigid-flexible coupling crystalline polymer for high-performance aqueous zinc-organic batteries. Chinese Chemical Letters, 2024, 35(9): 109803-. doi: 10.1016/j.cclet.2024.109803
14. [14]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
15. [15]
  Zeyu Jiang , Yadi Wang , Changwei Chen , Chi He . Progress and challenge of functional single-atom catalysts for the catalytic oxidation of volatile organic compounds. Chinese Chemical Letters, 2024, 35(9): 109400-. doi: 10.1016/j.cclet.2023.109400
16. [16]
  Yanrui Liu , Paramaguru Ganesan , Peng Gao . Harnessing d-f transition rare earth complexes for single layer white organic light emitting diodes. Chinese Journal of Structural Chemistry, 2024, 43(9): 100369-100369. doi: 10.1016/j.cjsc.2024.100369
17. [17]
  Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
18. [18]
  Xiangan Song , Shaogang Shen , Mengyao Lu , Ying Wang , Yong Zhang . Trifluoromethyl enable high-performance single-emitter white organic light-emitting devices based on quinazoline acceptor. Chinese Chemical Letters, 2024, 35(4): 109118-. doi: 10.1016/j.cclet.2023.109118
19. [19]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
20. [20]
  Qihan Lin , Jiabin Xing , Yue-Yang Liu , Gang Wu , Shi-Jia Liu , Hui Wang , Wei Zhou , Zhan-Ting Li , Dan-Wei Zhang . taBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine. Chinese Chemical Letters, 2024, 35(5): 109119-. doi: 10.1016/j.cclet.2023.109119

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(263)
HTML views(19)

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