Citation: Liu Qingqing, Zhang Yihan, Gao Can, Wang Tianyu, Hu Wenping, Dong Huanli. Synthesis and Property Study of Field-effect Emissive Conjugated Polymers Based on Styrene and Benzothiadiazole[J]. Acta Chimica Sinica, ;2020, 78(9): 945-953. doi: 10.6023/A20050170 shu

Synthesis and Property Study of Field-effect Emissive Conjugated Polymers Based on Styrene and Benzothiadiazole

Liu Qingqing ^a,b ,
Zhang Yihan ^a,b ,
Gao Can ^a ,
Wang Tianyu ^a ,
Hu Wenping ^a,c ,
Dong Huanli ^a,b,,

a.
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, School of Science, Tianjin University, Tianjin 300072, China

Corresponding author: Dong Huanli, dhl522@iccas.ac.cn
Received Date: 16 May 2020
Available Online: 24 June 2020
Fund Project: Beijing National Laboratory for Molecular Sciences BNLMS-CXXM-202012the National Natural Science Foundation of China 51725304Project supported by the National Key Research and Development Project (Nos. 2017YFA0204503, 2018YFA0703200), the National Natural Science Foundation of China (Nos. 61890943, 51725304) and Beijing National Laboratory for Molecular Sciences (BNLMS-CXXM-202012)the National Natural Science Foundation of China 61890943the National Key Research and Development Project 2018YFA0703200the National Key Research and Development Project 2017YFA0204503

Figures(7)

Conjugated polymer materials with good photoelectric performance, solution processing ability and flexibility are widely used as active layers in optoelectronic devices. Here, using Stille and Suzuki coupling reactions, we designed and synthesized two new conjugated polymers, poly(1,2-bis(2,5-bis(iso-octyloxy)phenylenevinylene-2,1,3-benzothiadiazole)) (PVBT) and poly(1,2-bis(2,5-bis(n-octyloxy)phenylenevinylene-2,1,3-benzothiadiazole)) (nPVBT), which contain structural element styrene fragments and an conjugated unit benzothiadiazole. Styrene fragments are conducive to luminescent properties of materials, such as phenylenevinylene (PPV) derivatives, while benzothiadiazole unit is electron withdrawing, and matches with many structural units of a donor. The conjugated polymers were characterized by gel permeation chromatography (GPC), elemental analysis and differential scanning calorimetry (DSC). The results indicate that each of these two polymers has good thermal stability. Their melting points were around 240~250℃ and decomposition temperatures around 380℃. Due to the presence of the structural alkoxy chains, these two polymers exhibit good solubility, which is conducive to solution-processed film formation. PVBT and nPVBT have strong fluorescence characters with maximum emission in the range of 590~605 nm. The photoluminescence quantum yield of these two polymers in dichloromethane solution (1×10^-5 mol·L^-1) is 23%~35%, and 12%~20% in solid films, which are annealed at 180℃ for 10 min. Due to benzothiadiazole's regulation of molecular energy levels, the highest occupied molecular orbital (HOMO) energy level of PVBT and nPVBT were modulated to be -5.73 and -5.61 eV, and the lowest unoccupied molecular orbital (LUMO) energy level were -3.37 and -3.32 eV, respectively. Typical p-type transporting property was determined by using PVBT and nPVBT films as active layers in organic field effect transistors. Because of the improved conjugation of the skeleton structures and the close packing between benzothiadiazole of main chains, these two conjugated polymers both exhibit efficient charge transport characteristics with saturation hole carrier mobility is up to 1.1×10^-4 cm²·V^-1·s^-1 and high switching on/off ratio of 10³~10⁴. This work provides new insight into the development of high-performance optoelectronic conjugated polymer materials and sheds light on the research of organic optoelectronic integrated devices.
- styrene,
- benzothiadiazole,
- strong emission,
- field-effect transporting property
1. [1]
  Huang, F.; Bo, Z. S.; Geng, Y. H.; Wang, X. H.; Wang, L. X.; Ma, Y. G.; Hou, J. H.; Hu, W. P.; Pei, J.; Dong, H. L.; Wang, S.; Li, Z.; Shuai, Z. G.; Li, Y. F.; Cao, Y. Acta Polym. Sin. 2019, 50, 988(in Chinese).
2. [2]
  Dong, H. L.; Fu, X. L.; Liu, J.; Wang, Z. R.; Hu, W. P. Adv. Mater. 2013, 25, 6158. doi: 10.1002/adma.201302514
3. [3]
  Xu, Y.; Yao, H. F.; Hou, J. H. Chin. J. Chem. 2019, 37, 207(in Chinese).
4. [4]
  Yang, C. Y.; Jin, W. L.; Wang, J.; Ding, Y. F.; Nong, S.; Shi, K.; Lu, Y.; Dai, Y. Z.; Zhuang, F. D.; Lei, T.; Di, C. A.; Zhu, D. B.; Wang, J. Y.; Pei, J. Adv. Mater. 2018, 30, 1802850. doi: 10.1002/adma.201802850
5. [5]
  Li, Q. Q.; Li, Z. Acc. Chem. Res. 2020, 53, 962. doi: 10.1021/acs.accounts.0c00060
6. [6]
  Thomas, T. H.; Harkin, D. J.; Gillett, A. J.; Lemaur, V.; Nikolka, M.; Sadhanala, A.; Richter, J. M.; Armitage, J.; Chen, H.; McCulloch, I.; Menke, S. M.; Olivier, Y.; Beljonne, D.; Sirringhaus, H. Nat. Commun. 2019, 10, 2614. doi: 10.1038/s41467-019-10277-y
7. [7]
  Feng, L. L.; Gu, P. C.; Dong, H. L.; Yao, Y. F.; Hu, W. P. Chin. Sci. Bull. 2015, 60, 2169(in Chinese).
8. [8]
  Ren, X. C.; Yang, F. X.; Gao, X.; Cheng, S. S.; Zhang, X. T.; Dong, H. L.; Hu, W. P. Adv. Energy Mater. 2018, 8, 1801003. doi: 10.1002/aenm.201801003
9. [9]
  Zheng, Z.; Ni, Z. J.; Zhang, X. T.; Zhen, Y. G.; Dong, H. L.; Zhang, J.; Hu, W. P. Sci. China Mater. 2019, 62, 813(in Chinese).
10. [10]
  Ni, Z. J.; Dong, H. L.; Wang, H. L.; Ding, S.; Zou, Y.; Zhao, Q.; Zhen, Y. G.; Liu, F.; Jiang, L.; Hu, W. P. Adv. Mater. 2018, 30, 1704843. doi: 10.1002/adma.201704843
11. [11]
  Ni, Z. J.; Wang, H. L.; Dong, H. L.; Dang, Y. F.; Zhao, Q.; Zhang, X. T.; Hu, W. P. Nat. Chem. 2019, 11, 271. doi: 10.1038/s41557-018-0200-y
12. [12]
  Guo, Y. L. Acta Polym. Sin. 2020, 51, 448(in Chinese).
13. [13]
  Yao, Y. F.; Dong, H. L.; Liu, F.; Russell, T. P.; Hu, W. P. Adv. Mater. 2017, 29, 1701251. doi: 10.1002/adma.201701251
14. [14]
  Zhao, S.; Zhu, R. Acta Chim. Sinica 2019, 77, 1250(in Chinese).
15. [15]
  Qiu, G. G.; Jiang, Z. Y.; Ni, Z. J.; Wang, H. L.; Dong, H. L.; Zhang, J. Q.; Zhang, X. T.; Shu, Z. B.; Lu, K.; Zhen, Y. G.; Wei, Z. X.; Hu, W. P. J. Mater. Chem. C 2017, 5, 566. doi: 10.1039/C6TC04271F
16. [16]
  Gu, P. C.; Hu, M. X.; Ding, S.; Zhao, G. Y.; Yao, Y. F.; Liu, F.; Zhang, X. T.; Dong, H. L.; Wang, X. K.; Hu, W. P. Chinese Chem. Lett. 2018, 29, 1675(in Chinese).
17. [17]
  Li, C. G.; Wang, Y. S.; Zou, Y.; Zhang, X. T.; Dong, H. L.; Hu, W. P. Angew. Chem. Int. Ed. 2020, 59, 9403. doi: 10.1002/anie.202002644
18. [18]
  Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263
19. [19]
  Dong, H. L.; Yan, Q. Q.; Hu, W. P. Acta Polym. Sin. 2017, 8, 1246(in Chinese).
20. [20]
  Qian, X.; Su, M.; Li, F. Y.; Song, Y. L. Acta Chim. Sinica 2016, 74, 565(in Chinese).
21. [21]
  Xu, X. N.; Han, B.; Yu, X.; Zhu, Y. Y. Acta Chim. Sinica 2019, 77, 485(in Chinese).
22. [22]
  Zhang, Y. H.; Ye, J.; Liu, Z. Y.; Liu, Q. Q.; Guo, X. F.; Dang, Y. F.; Zhang, J. Q.; Wei, Z. X.; Wang, Z. X.; Wang, Z. H.; Dong, H. L.; Hu, W. P. J. Mater. Chem. C 2020, DOI:10.1039/D0TC01174F. doi: 10.1039/D0TC01174F
23. [23]
  Fu, Y.; Wang, F.; Zhang, Y.; Fang, X.; Lai, W. Y.; Huang, W. Acta Chim. Sinica 2014, 72, 158(in Chinese).
24. [24]
  Wang, Z. W.; Guo, S. J.; Li, H. W.; Wang, B.; Sun, Y. T.; Xu, Z. Y.; Chen, X. S.; Wu, K. J.; Zhang, X. T.; Xing, F. F.; Li, L. Q.; Hu, W. P. Adv. Mater. 2019, 31, 1805630.
25. [25]
  Hepp, A.; Heil, H.; Weise, W.; Ahles, M.; Schmechel, R.; Seggern, H. V. Phys. Rev. Lett. 2003, 91, 157406. doi: 10.1103/PhysRevLett.91.157406
26. [26]
  Zhang, C. C.; Chen, P. L.; Hu, W. P. Small 2016, 12, 1252. doi: 10.1002/smll.201502546
27. [27]
  Muhieddine, K.; Ullah, M.; Pal, B. N.; Burn, P.; Namdas, E. B. Adv. Mater. 2014, 26, 6410. doi: 10.1002/adma.201400938
28. [28]
  Qin, Z. S.; Gao, H. K.; Liu, J. Y.; Zhou, K.; Li, J.; Dang, Y. Y.; Huang, L.; Deng, H. X.; Zhang, X. T.; Dong, H. L.; Hu, W. P. Adv. Mater. 2019, 31, 1903175. doi: 10.1002/adma.201903175
29. [29]
  Liu, C. F.; Liu, X.; Lai, W. Y.; Huang, W. Adv. Mater. 2018, 30, 1802466. doi: 10.1002/adma.201802466
30. [30]
  Ma, Y. G.; Shen, J. C. Sci. Sin. Chim. 2007, 37, 105(in Chinese).
31. [31]
  Zhang, X. T.; Dong, H. L.; Hu, W. P. Adv. Mater. 2018, 30, 1801048. doi: 10.1002/adma.201801048
32. [32]
  Xie, Z. Y.; Liu, D.; Zhang, Y. H.; Liu, Q. Q.; Dong, H. L.; Hu, W. P. Chem. J. Chin. Univ. 2020, 41, 1179(in Chinese).
33. [33]
  Liu, D.; De, J. B.; Gao, H. K.; Ma, S. Q.; Ou, Q.; Li, S.; Qin, Z. S.; Dong, H. L.; Liao, Q.; Xu, B.; Peng, Q.; Shuai, Z. G.; Tian, W. J.; Fu, H. B.; Zhang, X. T.; Zhen, Y. G.; Hu, W. P. J. Am. Chem. Soc. 2020, 142, 6332. doi: 10.1021/jacs.0c00871
34. [34]
  Liu, H. C.; Yao, L.; Li, B.; Chen, X. K.; Gao, Y.; Zhang, S. T.; Li, W. J.; Lu, P.; Yang, B.; Ma, Y. G. Chem. Commun. 2016, 52, 7356. doi: 10.1039/C6CC01993E
35. [35]
  Chen, M. Y.; Zhao, Y.; Yan, L. J.; Yang, S.; Zhu, Y. N.; Murtaza, I.; He, G. F.; Meng, H.; Huang, W. Angew. Chem. Int. Ed. 2016, 128, 1. doi: 10.1002/ange.201510990
36. [36]
  Chen, Z. K.; Lee, N. H. S.; Huang, W. Macromolecules 2003, 36, 1009. doi: 10.1021/ma021221n
37. [37]
  Burroughes, J. H.; Bradley, D. D. C.; Brown, A.; Marks, R. R.N.; Mackay, K.; Friend, R. H.; Burnst, P. L.; Holmest A. B. Nature 1990, 347, 539. doi: 10.1038/347539a0
38. [38]
  Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789. doi: 10.1126/science.270.5243.1789
39. [39]
  Tessler, N.; Denton, G. J.; Friend, R. H. Nature 1996, 382, 695. doi: 10.1038/382695a0
40. [40]
  Zaumseil, J.; Friend, R. H.; Sirringhaus, H. Nat. Mater. 2006, 5, 69. doi: 10.1038/nmat1537
41. [41]
  Gambino, S.; Bansal, A. K.; Samuel, I. D. W. Org. Electron. 2013, 14, 1980. doi: 10.1016/j.orgel.2013.03.038
42. [42]
  Johansson, D. M.; Theander, M.; Srdanov, G.; Yu, G.; Inganas, O.; Andersson, M. R. Macromolecules 2001, 34, 3716. doi: 10.1021/ma001921x
43. [43]
  Anant, P.; Lucas, N. T.; Jacob, J. Org. Lett. 2008, 10, 5533. doi: 10.1021/ol8022837
44. [44]
  Zhang, W. M.; Smith, J.; Watkins, S. E.; Gysel, R.; McGehee M.; Salleo, A.; Kirkpatrick, J.; Ashraf, S.; Anthopoulos, T.; Heeney, M.; McCulloch, I. J. Am. Chem. Soc. 2010, 132, 11437. doi: 10.1021/ja1049324
45. [45]
  Wen, S. P.; Pei, J. N.; Zhou, Y. H.; Li, P. F.; X, L. L.; Li, Y. W.; Xu, B.; Tian, W. J. Macromolecules 2009, 42, 4977. doi: 10.1021/ma900598c
46. [46]
  Gwinner, M. C.; Kabra, D.; Roberts, M.; Brenner, T. J. K.; Wallikewitz, B. H.; McNeill, C. R.; Friend, R. H.; Sirringhaus, H. Adv. Mater. 2012, 24, 2728. doi: 10.1002/adma.201104602
47. [47]
  Lei, T.; Dou, J. H.; Pei, J. Adv. Mater. 2012, 24, 6457. doi: 10.1002/adma.201202689
48. [48]
  Shahid, M.; Ashraf, R. S.; Klemm, E.; Sensfuss, S. Macromolecules 2006, 39, 7844. doi: 10.1021/ma061231e
49. [49]
  Li, Y. F.; Cao, Y.; Gao, J.; Wang, D. L.; Yu, G.; Heeger, A. J. Synthetic Met. 1999, 99, 243. doi: 10.1016/S0379-6779(99)00007-7
50. [50]
  Sirringhaus, H. Adv. Mater. 2014, 26, 1319. doi: 10.1002/adma.201304346
51. [51]
  Rivnay, J. M. S. C.; Miller, C. E.; Salleo, A.; Toney, M. F. Chem. Rev. 2012, 112, 5488. doi: 10.1021/cr3001109
1. [1]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
2. [2]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
3. [3]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
4. [4]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
5. [5]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
6. [6]
  Yujia LI , Tianyu WANG , Fuxue WANG , Chongchen WANG . Direct Z-scheme MIL-100(Fe)/BiOBr heterojunctions: Construction and photo-Fenton degradation for sulfamethoxazole. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 481-495. doi: 10.11862/CJIC.20230314
7. [7]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
8. [8]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
9. [9]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
10. [10]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
11. [11]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
12. [12]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
13. [13]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
14. [14]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
15. [15]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
16. [16]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
17. [17]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030
18. [18]
  Doudou Qin , Junyang Ding , Chu Liang , Qian Liu , Ligang Feng , Yang Luo , Guangzhi Hu , Jun Luo , Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034
19. [19]
  Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060
20. [20]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(2218)
HTML views(285)

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