Citation: Yuqing Ding, Zhiying Yi, Zhihui Wang, Hongyu Chen, Yan Zhao. Liquid nitrogen post-treatment for improved aggregation and electrical properties in organic semiconductors[J]. Chinese Chemical Letters, ;2024, 35(12): 109918. doi: 10.1016/j.cclet.2024.109918 shu

Liquid nitrogen post-treatment for improved aggregation and electrical properties in organic semiconductors

Yuqing Ding ^a ,
Zhiying Yi ^a ,
Zhihui Wang ^{a, b, *,} ,
Hongyu Chen ^{c, *,} ,
Yan Zhao ^{a, *,}

a.
Laboratory of Molecular Materials and Devices, Department of Materials Science, Fudan University, Shanghai 200433, China
b.
Department of Pathology, Changhai Hospital, Naval Medical University, Shanghai 200433, China
c.
Second Medical Center & National Clinical Research Center for Geriatric Diseases, Chinese People’s Liberation Army General Hospital, Beijing 100853, China

zh_wang@fudan.edu.cn

chenhy0528@163.com

zhaoy@fudan.edu.cn

Received Date: 20 February 2024
Revised Date: 19 April 2024
Accepted Date: 23 April 2024
Available Online: 24 April 2024

Figures(5)

Organic semiconductors are promising candidates as active layers in flexible and biocompatible electronics owing to their solution processability and molecular design flexibility. However, it remains necessary to establish a green processing approach to acquire desirable electrical properties for scalable industrial applications. Here, a highly efficient and environmentally friendly post-treatment method using liquid nitrogen as a cooling bath is developed to optimize the aggregation structure and electrical performance of organic semiconductors. The carrier mobility has increased by nearly 60% with this treatment, achieving a performance boost comparable to that of traditional annealing methods. This performance improvement is attributable to the denser aggregation structure and enhanced molecular ordering compared with those of as-cast semiconducting polymer films. Impressively, the entire process can be completed within a few minutes without additional vacuum or high-temperature conditions, offering an economical and efficient alternative to traditional methods. Furthermore, the enhancement effect and long-term stability of this treatment are validated across a wide range of organic semiconductors, positioning this green and versatile approach as a promising substitute for conventional post-treatment, thereby facilitating the development of next-generation sustainable electronics.
- Organic electronics,
- Environmentally friendly process,
- Ultralow-temperature post-treatment,
- Charge carrier mobility,
- Semiconducting polymer,
- Organic small molecule
1. [1]
  H. Chen, W. Zhang, M. Li, et al., Chem. Rev. 120 (2020) 2879–2949. doi: 10.1021/acs.chemrev.9b00532
2. [2]
  J. Chen, W. Zhang, L. Wang, G. Yu, Adv. Mater. 35 (2023) 2210772. doi: 10.1002/adma.202210772
3. [3]
  Y. Zheng, H. Li, T. Jiang, et al., Chin. Chem. Lett. 35 (2024) 108796. doi: 10.1016/j.cclet.2023.108796
4. [4]
  L. Yang, Y. Wu, Y. Yan, et al., Adv. Funct. Mater. 32 (2022) 2202456. doi: 10.1002/adfm.202202456
5. [5]
  Q. Chen, Y. Zhao, Y. Liu, Chin. Chem. Lett. 32 (2021) 3705–3717. doi: 10.1016/j.cclet.2021.05.043
6. [6]
  W. Huang, Y. Zhang, M. Song, et al., Chin. Chem. Lett. 33 (2022) 2281–2290. doi: 10.1016/j.cclet.2021.08.086
7. [7]
  Y. Sun, Y. Guo, Y. Liu, Mater. Sci. Eng. R: Rep. 136 (2019) 13–26. doi: 10.1016/j.mser.2018.10.003
8. [8]
  M. Nikolka, I. Nasrallah, B. Rose, et al., Nat. Mater. 16 (2017) 356–362. doi: 10.1038/nmat4785
9. [9]
  Y. Gao, J. Zhang, D. Liu, et al., Chin. Chem. Lett. 35 (2024) 108582. doi: 10.1016/j.cclet.2023.108582
10. [10]
  A. Mandal, S. Mandal, S.P. Verma, et al., Adv. Mater. Interfaces 10 (2023) 2202293. doi: 10.1002/admi.202202293
11. [11]
  Y. Sun, J. Peng, Y. Chen, et al., Sci. Rep. 7 (2017) 46193. doi: 10.1038/srep46193
12. [12]
  X. Ma, X. Dai, L. Xiang, et al., Chin. Chem. Lett. 35 (2024) 108734. doi: 10.1016/j.cclet.2023.108734
13. [13]
  D.H. Kang, S.Y. Kim, J.W. Lee, N.G. Park, J. Mater. Chem. A 9 (2021) 3441–3450. doi: 10.1039/D0TA10581C
14. [14]
  T. Wu, X.L. Shi, W.D. Liu, et al., Macromol. Mater. Eng. 307 (2022) 2200411. doi: 10.1002/mame.202200411
15. [15]
  K. Chen, N. Xue, G. Liu, et al., Chin. Chem. Lett. 34 (2023) 107884. doi: 10.1016/j.cclet.2022.107884
16. [16]
  Z. Xu, Y. Ni, H. Han, et al., Chin. Chem. Lett. 34 (2023) 107292. doi: 10.1016/j.cclet.2022.03.015
17. [17]
  D. Kawaguchi, Polym. J. 55 (2023) 1237–1245. doi: 10.1038/s41428-023-00820-6
18. [18]
  S. Wang, X. Zhao, C. Zhang, et al., Adv. Mater. 33 (2021) 2101633. doi: 10.1002/adma.202101633
19. [19]
  Y. Yang, J. Wang, Y. Zu, et al., Joule 7 (2023) 545–557. doi: 10.1016/j.joule.2023.02.013
20. [20]
  B. Qiu, Z. Chen, S. Qin, et al., Adv. Mater. 32 (2020) 1908373. doi: 10.1002/adma.201908373
21. [21]
  J. Liu, J. Garcia, L.M. Leahy, et al., Adv. Funct. Mater. 33 (2023) 2214196. doi: 10.1002/adfm.202214196
22. [22]
  T. Shen, W. Li, Y. Zhao, et al., Adv. Mater. 35 (2023) 2210093. doi: 10.1002/adma.202210093
23. [23]
  Q. Zhou, Z. Wang, Y. Yan, et al., npj Flex. Electron. 7 (2023) 35. doi: 10.1038/s41528-023-00269-w
24. [24]
  J. Xu, X. Liu, H. Wang, et al., Solid-State Electron. 127 (2017) 61–64. doi: 10.1016/j.sse.2016.11.003
25. [25]
  J. Xu, X. Liu, W. Hou, et al., Bull. Mater. Sci. 41 (2018) 111. doi: 10.1007/s12034-018-1618-y
26. [26]
  P. Kumar, S. Yadav, N. Kumar, L. Kumar, Solid-State Electron. 176 (2021) 107954. doi: 10.1016/j.sse.2020.107954
27. [27]
  D. Trefz, Y.M. Gross, C. Dingler, et al., Macromolecules 52 (2019) 43–54. doi: 10.1021/acs.macromol.8b02176
28. [28]
  H. Shan, J. He, B. Zhu, et al., J. Mater. Chem. C 10 (2022) 17583–17593. doi: 10.1039/D2TC02121H
29. [29]
  J. Wu, H. Zhu, C. Wu, et al., Solid-State Electron. 194 (2022) 108384. doi: 10.1016/j.sse.2022.108384
30. [30]
  H. Chen, T. Zhao, L. Li, et al., Adv. Mater. 33 (2021) 2102778. doi: 10.1002/adma.202102778
31. [31]
  X. Huang, L. Deng, F. Liu, et al., Energy Mater. Adv. 2021 (2021).
32. [32]
  K. Janus, D. Chlebosz, A. Janke, et al., Macromolecules 56 (2023) 964–973. doi: 10.1021/acs.macromol.2c01998
33. [33]
  J. Rivnay, M.F. Toney, Y. Zheng, et al., Adv. Mater. 22 (2010) 4359–4363. doi: 10.1002/adma.201001202
34. [34]
  Y. Li, P. Sonar, S.P. Singh, et al., J. Am. Chem. Soc. 133 (2011) 2198–2204. doi: 10.1021/ja1085996
35. [35]
  J. Kim, T.M. Swager, Nature 411 (2001) 1030–1034. doi: 10.1038/35082528
36. [36]
  M. Li, A.H. Balawi, P.J. Leenaers, et al., Nat. Commun. 10 (2019) 2867. doi: 10.1038/s41467-019-10519-z
37. [37]
  P.J. Brown, D.S. Thomas, A. Köhler, et al., Phys. Rev. B 67 (2003) 064203. doi: 10.1103/PhysRevB.67.064203
38. [38]
  B.S. Ong, Y. Wu, P. Liu, S. Gardner, Adv. Mater. 17 (2005) 1141–1144. doi: 10.1002/adma.200401660
39. [39]
  S.Y. Son, Y. Kim, J. Lee, et al., J. Am. Chem. Soc. 138 (2016) 8096–8103. doi: 10.1021/jacs.6b01046
40. [40]
  E.J. Bailey, K.I. Winey, Prog. Polym. Sci. 105 (2020) 101242. doi: 10.1016/j.progpolymsci.2020.101242
41. [41]
  Z. Wang, Y. Wu, Q. Zhou, et al., Matter 6 (2023) 3434–3448. doi: 10.1016/j.matt.2023.05.042
42. [42]
  R.P. White, J.E.G. Lipson, Macromolecules 49 (2016) 3987–4007. doi: 10.1021/acs.macromol.6b00215
1. [1]
  Brandon Bishop , Shaofeng Huang , Hongxuan Chen , Haijia Yu , Hai Long , Jingshi Shen , Wei Zhang . Artificial transmembrane channel constructed from shape-persistent covalent organic molecular cages capable of ion and small molecule transport. Chinese Chemical Letters, 2024, 35(11): 109966-. doi: 10.1016/j.cclet.2024.109966
2. [2]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244
3. [3]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
4. [4]
  Yunjie Dang , Yanru Feng , Xiao Chen , Chaoxing He , Shujie Wei , Dingyang Liu , Jinlong Qi , Huaxing Zhang , Shaokun Yang , Zhiyun Niu , Bai Xiang . Development of a multi-level pH-responsive lipid nanoplatform for efficient co-delivery of siRNA and small-molecule drugs in tumor treatment. Chinese Chemical Letters, 2024, 35(12): 109660-. doi: 10.1016/j.cclet.2024.109660
5. [5]
  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
6. [6]
  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
7. [7]
  Fereshte Hassanzadeh-Afruzi , Mina Azizi , Iman Zare , Ehsan Nazarzadeh Zare , Anwarul Hasan , Siavash Iravani , Pooyan Makvandi , Yi Xu . Advanced metal-organic frameworks-polymer platforms for accelerated dermal wound healing. Chinese Chemical Letters, 2024, 35(11): 109564-. doi: 10.1016/j.cclet.2024.109564
8. [8]
  Ting Shi , Ziyang Song , Yaokang Lv , Dazhang Zhu , Ling Miao , Lihua Gan , Mingxian Liu . Hierarchical porous carbon guided by constructing organic-inorganic interpenetrating polymer networks to facilitate performance of zinc hybrid supercapacitors. Chinese Chemical Letters, 2025, 36(1): 109559-. doi: 10.1016/j.cclet.2024.109559
9. [9]
  Wenbiao Zhang , Bolong Yang , Zhonghua Xiang . Atomically dispersed Cu-based metal-organic framework directly for alkaline polymer electrolyte fuel cells. Chinese Chemical Letters, 2025, 36(2): 109630-. doi: 10.1016/j.cclet.2024.109630
10. [10]
  Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
11. [11]
  Yaxian Liang , Qingyi Li , Liwei Hu , Ruohan Zhai , Fan Liu , Lin Tan , Xiaofei Wang , Huixu Xie . Environmentally friendly polylysine gauze dressing for an innovative antimicrobial approach to infected wound management. Chinese Chemical Letters, 2024, 35(10): 109459-. doi: 10.1016/j.cclet.2023.109459
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]
  Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
15. [15]
  Ping Liu , Fei Yu . Covalent organic framework ionomers for medium-temperature fuel cells. Chinese Journal of Structural Chemistry, 2025, 44(4): 100465-100465. doi: 10.1016/j.cjsc.2024.100465
16. [16]
  Xue-Zhi Wang , Yi-Tong Liu , Chuang-Wei Zhou , Bei Wang , Dong Luo , Mo Xie , Meng-Ying Sun , Yong-Liang Huang , Jie Luo , Yan Wu , Shuixing Zhang , Xiao-Ping Zhou , Dan Li . Amplified circularly polarized luminescence of chiral metal-organic frameworks via post-synthetic installing pillars. Chinese Chemical Letters, 2024, 35(10): 109380-. doi: 10.1016/j.cclet.2023.109380
17. [17]
  Jieqiong Xu , Wenbin Chen , Shengkai Li , Qian Chen , Tao Wang , Yadong Shi , Shengyong Deng , Mingde Li , Peifa Wei , Zhuo Chen . Organic stoichiometric cocrystals with a subtle balance of charge-transfer degree and molecular stacking towards high-efficiency NIR photothermal conversion. Chinese Chemical Letters, 2024, 35(10): 109808-. doi: 10.1016/j.cclet.2024.109808
18. [18]
  Aolei Tan , Xiaoxiao Ma . Exploring the functional roles of small-molecule metabolites in disease research: Recent advancements in metabolomics. Chinese Chemical Letters, 2024, 35(8): 109276-. doi: 10.1016/j.cclet.2023.109276
19. [19]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
20. [20]
  Feifei Wang , Hang Yao , Xinyue Wu , Yijian Tang , Yang Bai , Hui Chong , Huan Pang . Metal–organic framework and its composites modulate macrophage polarization in the treatment of inflammatory diseases. Chinese Chemical Letters, 2024, 35(5): 108821-. doi: 10.1016/j.cclet.2023.108821

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(251)
HTML views(7)

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