Citation: Ying Yang, Tong Shan, Jian Cao, Hua-Chun Wang, Ji-Kang Wang, Hong-Liang Zhong, Yun-Xiang Xu. Unsymmetric Side Chains of Indacenodithiophene Copolymers Lead to Improved Packing and Device Performance[J]. Chinese Journal of Polymer Science, ;2020, 38(4): 342-348. doi: 10.1007/s10118-020-2342-9 shu

Unsymmetric Side Chains of Indacenodithiophene Copolymers Lead to Improved Packing and Device Performance

Ying Yang ^a,† ,
Tong Shan ^b,† ,
Jian Cao ^a ,
Hua-Chun Wang ^a ,
Ji-Kang Wang ^a ,
Hong-Liang Zhong ^b,, ,
Yun-Xiang Xu ^a,,

a.
College of Polymer Science & Engineering, State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu 610065, China
b.
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Hong-Liang Zhong, hlzhong@sjtu.edu.cn Yun-Xiang Xu, yxxu@scu.edu.cn
Received Date: 23 July 2019
Revised Date: 20 August 2019
Available Online: 24 October 2019

Two conjugated polymers (PuIDTBD and PuIDTQ) with unsymmetric side chains have been prepared for polymer solar cells using two other polymers (PIDTBD and PIDTQ) with symmetric side chains as control compounds. The combination of methyl and 4-hexylphenyl side chains on the same bridged carbon can ensure good solubility, decrease π-π stacking distances, and bring proper miscibility with PC₇₁BM simultaneously. Therefore, the corresponding polymer solar cells (PSCs) based on donor polymers with unsymmetric side chains exhibited enhanced short-circuit current density (J_SC) and power conversion efficiency (PCE) compared with those of control polymers. The PIDTBD and PIDTQ based devices possessed low PCE of 2.13% and 1.48%, while PCEs of devices based on PuIDTBD and PuIDTQ were improved to 3.93% and 4.12%, respectively. The results demonstrate that unsymmetric side chain engineering of conjugated polymers is an effective approach to achieve high performance PSCs.
- Polymer solar cell,
- Indacenodithiophene,
- Side-chain engineering,
- Unsymmetric
1. [1]
  Wang, G.; Melkonyan, F. S.; Facchetti, A.; Marks, T. J. All-polymer solar cells: recent progress, challenges, and prospects. Angew. Chem. Int. Ed. 2019, 58, 4129−4142. doi: 10.1002/anie.201808976
2. [2]
  Zhao, W.; Qian, D.; Zhang, S.; Li, S.; Inganäs, O.; Gao, F.; Hou, J. Fullerene-free polymer solar cells with over 11% efficiency and excellent thermal stability. Adv. Mater. 2016, 28, 4734−4739. doi: 10.1002/adma.201600281
3. [3]
  Yang, B.; Zhang, S.; Chen, Y.; Cui, Y.; Liu, D.; Yao, H.; Zhang, J.; Wei, Z.; Hou, J. Investigation of conjugated polymers based on naphtho[2,3-c]thiophene-4,9-dione in fullerene-based and fullerene-free polymer solar cells. Macromolecules 2017, 50, 1453−1462. doi: 10.1021/acs.macromol.6b02733
4. [4]
  Sun, C.; Pan, F.; Bin, H.; Zhang, J.; Xue, L.; Qiu, B.; Wei, Z.; Zhang, Z. G.; Li, Y. A low cost and high performance polymer donor material for polymer solar cells. Nat. Commun. 2018, 9, 743. doi: 10.1038/s41467-018-03207-x
5. [5]
  Scharber, M. C. On the efficiency limit of conjugated polymer: fullerene-based bulk heterojunction solar cells. Adv. Mater. 2016, 28, 1994−2001. doi: 10.1002/adma.201504914
6. [6]
  Shi, Z.; Bai, Y.; Chen, X.; Zeng, R.; Tan, Z. A. Tandem structure: A breakthrough in power conversion efficiency for highly efficient polymer solar cells. Sustain. Energy Fuels 2019, 3, 910−934. doi: 10.1039/C8SE00601F
7. [7]
  Chochos, C. L.; Drakopoulou, S.; Katsouras, A.; Squeo, B. M.; Sprau, C.; Colsmann, A.; Gregoriou, V. G.; Cando, A. P.; Allard, S.; Scherf, U.; Gasparini, N.; Kazerouni, N.; Ameri, T.; Brabec, C. J.; Avgeropoulos, A. Beyond donor-acceptor (D-A) approach: Structure-optoelectronic properties—organic photovoltaic performance correlation in new D-A1-D-A2 low-bandgap conjugated polymers. Macromol. Rapid Commun. 2017, 38, 1600720. doi: 10.1002/marc.201600720
8. [8]
  Guo, X.; Baumgarten, M.; Müllen, K. Designing π-conjugated polymers for organic electronics. Prog. Polym. Sci. 2013, 38, 1832−1908. doi: 10.1016/j.progpolymsci.2013.09.005
9. [9]
  Chochos, C. L.; Singh, R.; Kim, M.; Gasparini, N.; Katsouras, A.; Kulshreshtha, C.; Gregoriou, V. G.; Keivanidis, P. E.; Ameri, T.; Brabec, C. J.; Cho, K.; Avgeropoulos, A. Enhancement of the power conversion efficiency in organic photovoltaics by unveiling the appropriate polymer backbone enlargement approach. Adv. Funct. Mater. 2016, 26, 1840−1848. doi: 10.1002/adfm.201504953
10. [10]
  Mahesh, K.; Karpagam, S.; Pandian, K. How to design donor-acceptor based heterocyclic conjugated polymers for applications from organic electronics to sensors. Top. Curr. Chem. 2019, 377, 12. doi: 10.1007/s41061-019-0237-4
11. [11]
  Wang, M.; Hu, X.; Liu, L.; Duan, C.; Liu, P.; Ying, L.; Huang, F.; Cao, Y. Design and synthesis of copolymers of indacenodithiophene and naphtho[1,2-c:5,6-c]bis(1,2,5-thiadiazole) for polymer solar cells. Macromolecules 2013, 46, 3950−3958. doi: 10.1021/ma400355w
12. [12]
  Yin, Y.; Zhang, Y.; Zhao, L. Indaceno-based conjugated polymers for polymer solar cells. Macromol. Rapid Commun. 2018, 39, 1700697. doi: 10.1002/marc.201700697
13. [13]
  Bronstein, H.; Leem, D. S.; Hamilton, R.; Woebkenberg, P.; King, S.; Zhang, W.; Ashraf, R. S.; Heeney, M.; Anthopoulos, T. D.; Mello, J. D.; McCulloch, I. Indacenodithiophene-co-benzothiadiazole copolymers for high performance solar cells or transistors via alkyl chain optimization. Macromolecules 2011, 44, 6649−6652. doi: 10.1021/ma201158d
14. [14]
  Ma, Y.; Kang, Z.; Zheng, Q. Recent advances in wide bandgap semiconducting polymers for polymer solar cells. J. Mater. Chem. A 2017, 5, 1860−1872. doi: 10.1039/C6TA09325F
15. [15]
  Qin, T.; Zang, Y.; Bai, W. Y.; Yao, K.; Xu, Y. X. The influence of oxygen atoms on conformation and π-π stacking of ladder-type donor-based polymers and their photovoltaic properties. Macromol. Rapid Commun. 2017, 38, 1700156. doi: 10.1002/marc.201700156
16. [16]
  Wang, H. C.; Li, Q. Y.; Yin, H. B.; Ren, X.; Yao, K.; Zheng, Y.; Xu, Y. X. Synergistic effects of selenophene and extended ladder-type donor units for efficient polymer solar cells. Macromol. Rapid Commun. 2018, 39, 1700483. doi: 10.1002/marc.201700483
17. [17]
  Xiao, Z.; Liu, F.; Geng, X.; Zhang, J.; Wang, S.; Xie, Y.; Li, Z.; Yang, H.; Yuan, Y.; Ding, L. A carbon-oxygen-bridged ladder-type building block for efficient donor and acceptor materials used in organic solar cells. Sci. Bull. 2017, 62, 1331−1336. doi: 10.1016/j.scib.2017.09.017
18. [18]
  Xu, Y. X.; Chueh, C. C.; Yip, H. L.; Ding, F. Z.; Li, Y. X.; Li, C. Z.; Li, X.; Chen, W. C.; Jen, A. K. Y. Improved charge transport and absorption coefficient in indacenodithieno[3,2-b]thiophene-based ladder-type polymer leading to highly efficient polymer solar cells. Adv. Mater. 2012, 24, 6356−6361. doi: 10.1002/adma.201203246
19. [19]
  Zhang, Z. G.; Li, Y. Side-chain engineering of high-efficiency conjugated polymer photovoltaic materials. Sci. China Chem. 2015, 58, 192−209. doi: 10.1007/s11426-014-5260-2
20. [20]
  Zhang, M.; Guo, X.; Wang, X.; Wang, H.; Li, Y. Synthesis and photovoltaic properties of D-A copolymers based on alkyl-substituted indacenodithiophene donor unit. Chem. Mater. 2011, 23, 4264−4270. doi: 10.1021/cm2019586
21. [21]
  Zhang, W.; Han, Y.; Zhu, X.; Fei, Z.; Feng, Y.; Treat, N. D.; Faber, H.; Stingelin, N.; McCulloch, I.; Anthopoulos, T. D.; Heeney, M. A novel alkylated indacenodithieno[3,2-b]thiophene-based polymer for high-performance field-effect transistors. Adv. Mater. 2016, 28, 3922−3927. doi: 10.1002/adma.201504092
22. [22]
  Zhang, X.; Bronstein, H.; Kronemeijer, A. J.; Smith, J.; Kim, Y.; Kline, R. J.; Richter, L. J.; Anthopoulos, T. D.; Sirringhaus, H.; Song, K.; Heeney, M.; Zhang, W.; McCulloch, I.; DeLongchamp, D. M. Molecular origin of high field-effect mobility in an indacenodithiophene-benzothiadiazole copolymer. Nat. Commun. 2013, 4, 2238. doi: 10.1038/ncomms3238
23. [23]
  Chochos, C. L.; Katsouras, A.; Gasparini, N.; Koulogiannis, C.; Ameri, T.; Brabec, C. J.; Avgeropoulos, A. Rational design of high-performance wide-bandgap (≈2 eV) polymer semiconductors as electron donors in organic photovoltaics exhibiting high open circuit voltages (≈ 1 V). Macromol. Rapid Commun. 2017, 38, 1600614. doi: 10.1002/marc.201600614
24. [24]
  Wang, M.; Cai, D.; Yin, Z.; Chen, S. C.; Du, C. F.; Zheng, Q. Asymmetric-indenothiophene-based copolymers for bulk heterojunction solar cells with 9.14% efficiency. Adv. Mater. 2016, 28, 3359−3365. doi: 10.1002/adma.201505957
25. [25]
  Liu, D.; Zhu, Q.; Gu, C.; Wang, J.; Qiu, M.; Chen, W.; Bao, X.; Sun, M.; Yang, R. High-performance photovoltaic polymers employing symmetry-breaking building blocks. Adv. Mater. 2016, 28, 8490−8498. doi: 10.1002/adma.201602857
26. [26]
  Bai, W.; Xu, X.; Li, Q.; Xu, Y.; Peng, Q. Efficient nonfullerene polymer solar cells enabled by small-molecular acceptors with a decreased fused-ring core. Small Methods 2018, 2, 1700373. doi: 10.1002/smtd.201700373
27. [27]
  Feng, S.; Zhang, C. E.; Liu, Y.; Bi, Z.; Zhang, Z.; Xu, X.; Ma, W.; Bo, Z. Fused-ring acceptors with asymmetric side chains for high-performance thick-film organic solar cells. Adv. Mater. 2017, 29, 1703527. doi: 10.1002/adma.201703527
28. [28]
  Cao, J.; Shan, T.; Wang, J. K.; Xu, Y. X.; Ren, X.; Zhong, H. Stereoisomerism of ladder-type acceptor molecules and its effect on photovoltaic properties. Dyes Pigments 2019, 165, 354−360. doi: 10.1016/j.dyepig.2019.02.046
29. [29]
  Song, C. E.; Kim, Y. J.; Suranagi, S. R.; Kini, G. P.; Park, S.; Lee, S. K.; Shin, W. S.; Moon, S. J.; Kang, I. N.; Park, C. E.; Lee, J. C. Impact of the crystalline packing structures on charge transport and recombination via alkyl chain tunability of DPP-based small molecules in bulk heterojunction solar cells. ACS Appl. Mater. Interfaces 2016, 8, 12940−12950. doi: 10.1021/acsami.6b01576
30. [30]
  Fan, J.; Zhang, Y.; Lang, C.; Qiu, M.; Song, J.; Yang, R.; Guo, F.; Yu, Q.; Wang, J.; Zhao, L. Side chain effect on poly(beznodithiophene-co-dithienobenzoquinoxaline) and their applications for polymer solar cells. Polymer 2016, 82, 228−237. doi: 10.1016/j.polymer.2015.11.052
31. [31]
  Liu, X.; Li, Q.; Li, Y.; Gong, X.; Su, S. J.; Cao, Y. Indacenodithiophene core-based small molecules with tunable side chains for solution-processed bulk heterojunction solar cells. J. Mater. Chem. A 2014, 2, 4004−4013. doi: 10.1039/c3ta14659f
32. [32]
  Liu, D.; Wang, J.; Gu, C.; Li, Y.; Bao, X.; Yang, R. Stirring up acceptor phase and controlling morphology via choosing appropriate rigid aryl rings as lever arms in symmetry-breaking benzodithiophene for high-performance fullerene and fullerene-free polymer solar cells. Adv. Mater. 2018, 30, 1705870. doi: 10.1002/adma.201705870
33. [33]
  Zhu, T.; Wan, Y.; Guo, Z.; Johnson, J.; Huang, L. Two birds with one stone: tailoring singlet fission for both triplet yield and exciton diffusion length. Adv. Mater. 2016, 28, 7539−7547. doi: 10.1002/adma.201600968
1. [1]
  Yunan Yuan , Zhimin Luo , Jie Chen , Chaoliang He , Kai Hao , Huayu Tian . Constructing thermoresponsive PNIPAM-based microcarriers for cell culture and enzyme-free cell harvesting. Chinese Chemical Letters, 2024, 35(7): 109549-. doi: 10.1016/j.cclet.2024.109549
2. [2]
  Yu ZHANG , Fangfang ZHAO , Cong PAN , Peng WANG , Liangming WEI . Application of double-side modified separator with hollow carbon material in high-performance Li-S battery. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1218-1232. doi: 10.11862/CJIC.20230412
3. [3]
  Supphachok Chanmungkalakul , Syed Ali Abbas Abedi , Federico J. Hernández , Jianwei Xu , Xiaogang Liu . The dark side of cyclooctatetraene (COT): Photophysics in the singlet states of “self-healing” dyes. Chinese Chemical Letters, 2024, 35(8): 109227-. doi: 10.1016/j.cclet.2023.109227
4. [4]
  Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
5. [5]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
6. [6]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
7. [7]
  Chi Li , Peng Gao . Is dipole the only thing that matters for inverted perovskite solar cells?. Chinese Journal of Structural Chemistry, 2024, 43(6): 100324-100324. doi: 10.1016/j.cjsc.2024.100324
8. [8]
  Tiankai Sun , Hui Min , Zongsu Han , Liang Wang , Peng Cheng , Wei Shi . Rapid detection of nanoplastic particles by a luminescent Tb-based coordination polymer. Chinese Chemical Letters, 2024, 35(5): 108718-. doi: 10.1016/j.cclet.2023.108718
9. [9]
  Mengjun Sun , Zhi Wang , Jvhui Jiang , Xiaobing Wang , Chuang Yu . Gelation mechanisms of gel polymer electrolytes for zinc-based batteries. Chinese Chemical Letters, 2024, 35(5): 109393-. doi: 10.1016/j.cclet.2023.109393
10. [10]
  Huimin Gao , Zhuochen Yu , Xuze Zhang , Xiangkun Yu , Jiyuan Xing , Youliang Zhu , Hu-Jun Qian , Zhong-Yuan Lu . A mini review of the recent progress in coarse-grained simulation of polymer systems. Chinese Journal of Structural Chemistry, 2024, 43(5): 100266-100266. doi: 10.1016/j.cjsc.2024.100266
11. [11]
  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
12. [12]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
13. [13]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
14. [14]
  Yang Liu , Yan Liu , Kaiyin Yang , Zhiruo Zhang , Wenbo Zhang , Bingyou Yang , Hua Li , Lixia Chen . A selective HK2 degrader suppresses SW480 cancer cell growth by degrading HK2. Chinese Chemical Letters, 2024, 35(8): 109264-. doi: 10.1016/j.cclet.2023.109264
15. [15]
  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
16. [16]
  Jing Chen , Peisi Xie , Pengfei Wu , Yu He , Zian Lin , Zongwei Cai . MALDI coupled with laser-postionization and trapped ion mobility spectrometry contribute to the enhanced detection of lipids in cancer cell spheroids. Chinese Chemical Letters, 2024, 35(4): 108895-. doi: 10.1016/j.cclet.2023.108895
17. [17]
  Yanjing Li , Jiayin Li , Yuqi Chang , Yunfeng Lin , Lei Sui . Tetrahedral framework nucleic acids promote the proliferation and differentiation potential of diabetic bone marrow mesenchymal stem cell. Chinese Chemical Letters, 2024, 35(9): 109414-. doi: 10.1016/j.cclet.2023.109414
18. [18]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
19. [19]
  Ying Gao , Rong Zhou , Qiwen Wang , Shaolong Qi , Yuanyuan Lv , Shuang Liu , Jie Shen , Guocan Yu . Natural killer cell membrane doped supramolecular nanoplatform with immuno-modulatory functions for immuno-enhanced tumor phototherapy. Chinese Chemical Letters, 2024, 35(10): 109521-. doi: 10.1016/j.cclet.2024.109521
20. [20]
  Shu-Ran Xu , Fang-Xing Xiao . Metal halide perovskites quantum dots: Synthesis, and modification strategies for solar CO2 conversion. Chinese Journal of Structural Chemistry, 2023, 42(12): 100173-100173. doi: 10.1016/j.cjsc.2023.100173

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4079)
HTML views(126)

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