Citation: Shi-fan Wang, Ya-nan Liu, Jie Yang, You-tian Tao, Yan Guo, Xu-dong Cao, Zhi-guo Zhang, Yong-fang Li, Wei Huang. Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells[J]. Chinese Journal of Polymer Science, ;2017, 35(2): 207-218. doi: 10.1007/s10118-017-1889-6 shu

Orthogonal Solubility in Fully Conjugated Donor-Acceptor Block Copolymers: Compatibilizers for Polymer/Fullerene Bulk-Heterojunction Solar Cells

Shi-fan Wang ^a ,
Ya-nan Liu ^a ,
Jie Yang ^a,b ,
You-tian Tao ^a,, ,
Yan Guo ^c ,
Xu-dong Cao ^a ,
Zhi-guo Zhang ^b,, ,
Yong-fang Li ^b ,
Wei Huang ^a,,

a.
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University (Nanjing Tech), Nanjing 211816, China
b.
Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
c.
Department of Biomedical Engineering, College of Engineering and Applied Sciences, Nanjing 210093, China

Corresponding author: You-tian Tao, iamyttao@njtech.edu.cn Zhi-guo Zhang, zgzhangwhu@iccas.ac.cn Wei Huang, iamwhuang@njtech.edu.cn
Received Date: 18 July 2016
Revised Date: 14 August 2016
Accepted Date: 15 August 2016

Fund Project: the National Natural Science Foundation of China 21304047Natural Science Foundation of Jiangsu Province 13KJB430017Research Fund for the Doctoral Program of Higher Education 20133221120015

Donor-acceptor (D-A) type fully conjugated block copolymer systems have been rarely reported due to the challenges in synthetic approaches to prepare well-defined low-polydispersity products. In this work, fully conjugated block copolymers are synthesized in a one-pot reaction through Stille coupling polycondensation, by utilizing the end-functional polymer copolymerization method. End-functional P3HT are copolymerized with AA (2, 7-dibromo-9-(heptadecan-9-yl)-9H-carbazole) and BB (4, 7-bis (5-(trimethylstannyl) thiophen-2-yl) benzo[c] [1, 2, 5]thiadiazole, TBT) type monomers, respectively. The orthogonal solubility between the very soluble P3HT donor and the insoluble PCDTBT acceptor block improves the purity of block copolymers as well as distinct nano-scale phase-separation compared with other reports on miscibility of donor and acceptor polymer block. Further purification via preparative GPC is carried out to remove the excess of unreacted P3HT and free PCDTBT as well as to achieve low polydispersity of block copolymers. The chemical structure of the P3HT-b-PCDTBT block copolymers are verified via ¹H-NMR, and further confirmed by FTIR spectra. The block copolymer shows broad absorption and moderate optical band gap of 1.8 eV. Furthermore, the fully conjugated block copolymer films exhibit significant fine structures, much smoother film morphology compared to P3HT/PCDTBT polymer blends. By adding a small amount of block copolymer P3HT-b-PCDTBT as a compatibilizer into the bulk-heterojunction of P3HT:PC₆₁BM blends, polymer solar cells with an 8% increase of short circuit current (J_sc) and 10% increase of power conversion efficiency (PCE) are achieved owing to the improvement of the active-layer film morphology. To the best of our knowledge, this is the first report on donor-acceptor type fully conjugated block copolymer as an effective ternary additive in polymer:fullerene bulk heterojunction solar cells.
- Block copolymers,
- Donor,
- Acceptor,
- Bulk heterojunction solar cells,
- Compatibilizer
1. [1]
  Yu, G., Gao J., Hummelen, J.C., Wudl, F. and Heeger, A.J., Science, 1995, 270:1789 doi: 10.1126/science.270.5243.1789
2. [2]
  M. Halls, J.J., Walsh, C.A., Greenham, N.C., Marseglia, E.A., Friend, R.H., Moratti, S.C. and Holmes, A.B., Nature, 1995, 376:498 doi: 10.1038/376498a0
3. [3]
  You, J., Dou, L., Yoshimura, K., Kato, T., Ohya, K., Moriarty, T., Emery, K., Chen, C.C., Gao, J., Li, G. and Yang, Y., Nat. Commun., 2013, 4:1446 doi: 10.1038/ncomms2411
4. [4]
  He, Z., Zhong, C., Su, S., Xu, M., Wu, H. and Cao, Y., Nat. Photon., 2012, 6:593 doi: 10.1038/nphoton.2012.190
5. [5]
  Keshtov, M.L., Marochkin, D.V., Fu, Y., Xie, Z., Geng, Y., Kochurov, V.S. and Khokhlov, A.R. Chinese J. Polym. Sci., 2014, 32:844 doi: 10.1007/s10118-014-1458-1
6. [6]
  Qian, M., Zhang, R., Hao, J., Zhang, W., Zhang, Q., Wang, J., Tao, Y., Chen, S., Fang, J. and Huang, W., Adv. Mater., 2015, 27:3546 doi: 10.1002/adma.v27.23
7. [7]
  Wang, S., Yang, J., Zhang, Z., Hu, Y., Cao, X., Li, H., Tao, Y., Li, Y. and Huang, W., RSC Adv., 2015, 5:68192 doi: 10.1039/C5RA07383A
8. [8]
  Slota, J.E., He, X. and Huck, W.T.S., Nano Today, 2010, 5:231 doi: 10.1016/j.nantod.2010.05.004
9. [9]
  Etxebarria, I., Ajuria, J. and Pacios, R., Org. Electron., 2015, 19:34 doi: 10.1016/j.orgel.2015.01.014
10. [10]
  Chan, S., Lai, C., Chen, H., Ting, C. And Chen, C.P., Macromolecules, 2011, 44:8886 doi: 10.1021/ma201425d
11. [11]
  Riede, M.K., Sylvester-Hvid, K.O., Glatthaar, M., Keegan, N., Ziegler, T., Zimmermann, B., Niggemann, M., Liehr, A.W., Willeke, G. and Gombert, A., Prog. Photovolt:Res. Appl., 2008, 16:561 doi: 10.1002/pip.v16:7
12. [12]
  Mulherin, R.C., Jung, S., Huettner, S., Johnson, K., Kohn, P., Sommer, M., Allard, S., Scherf, U. and Greenham, N.C., Nano Lett., 2011, 11:4846 doi: 10.1021/nl202691n
13. [13]
  Chang, L., Lademann, H.W.A., Bonekamp, J.B., Meerholz, K. and Moulé, A.J., Adv. Funct. Mater., 2011, 21:1779 doi: 10.1002/adfm.201002372
14. [14]
  Pavlopoulou, E., Kim, C.S., Lee, S.S., Chen, Z., Facchetti, A., Toney, M.F. and Loo, Y., Chem. Mater., 2014, 26:5020 doi: 10.1021/cm502112z
15. [15]
  Lou, S.J., Szarko, J.M., Xu, T., Yu, L., Marks, T.J. and Chen, L.X., J. Am. Chem. Soc., 2011, 133:20661 doi: 10.1021/ja2085564
16. [16]
  Padinger, F., Rittberger, R.S. and Sariciftci, N.S., Adv. Funct. Mater., 2003, 13:85 doi: 10.1002/adfm.200390011
17. [17]
  Saeki, A., Yoshikawa, S., Tsuji, M., Koizumi, Y., Ide, M., Vijayakumar, C. and Seki, S., J. Am. Chem. Soc., 2012, 134:19035 doi: 10.1021/ja309524f
18. [18]
  Robb, M.J., Ku, S. and Hawker, C.J., Adv. Mater., 2013, 25:5686 doi: 10.1002/adma.v25.40
19. [19]
  Lai, Y., Ohshimizu, K., Takahashi, A., Hsu, J., Higashihara, T., Ueda, M. And Chen, W., J. Polym. Sci., Part A:Polym. Chem., 2011, 49:2577
20. [20]
  Wang, J. and Higashihara, T., Polym. Chem., 2013, 4:5518 doi: 10.1039/c3py00979c
21. [21]
  Scherf, U., Gutacker, A. and Koenen, N., Acc. Chem. Res., 2008, 41:1086 doi: 10.1021/ar7002539
22. [22]
  Lee, Y. and Gomez, E.D., Macromolecules, 2015, 48:7385 doi: 10.1021/acs.macromol.5b00112
23. [23]
  Wang, S., Guo, Y., Yang, J., Tao, Y. and Huang, W., Chin. J. Chem., 2015, 33:865 doi: 10.1002/cjoc.201500257
24. [24]
  Ku, S.Y., Brady, M.A., Treat, N.D., Cochran, J.E., Robb, M.J., Kramer, E.J., Chabinyc, M.L. and Hawker, C.J., J. Am. Chem. Soc., 2012, 134:16040 doi: 10.1021/ja307431k
25. [25]
  Guo, C., Lin, Y.H., Witman, M.D., Smith, K.A., Wang, C., Hexemer, A., Strzalka, J., Gomez, E.D. and Verduzco, R., Nano Lett., 2013, 13:2957 doi: 10.1021/nl401420s
26. [26]
  Bolag, A., Hayashi, H., Charbonnaz, P., Sakai N. and Matile, S., Chemistry Open, 2013, 2:55
27. [27]
  Jea Uk, L., Jae Woong, J., Todd, E., Thomas, P.R. and Won Ho, J., Nanotechnology, 2010, 21:105201 doi: 10.1088/0957-4484/21/10/105201
28. [28]
  Rajaram, S., Armstrong, P.B., Kim, B.J. and Fréchet, J.M.J., Chem. Mater., 2009, 21:1775 doi: 10.1021/cm900911x
29. [29]
  Wang, S., Yang, Q., Tao, Y., Guo, Y., Yang, J., Liu, Y., Zhao, L., Xie, Z. and Huang, W., New J. Chem., 2016, 40:1825 doi: 10.1039/C5NJ02636A
30. [30]
  Mok, W., Lin, Y., Yager, K.G., Mohite, A.D., Nie, W., Darling, S.B., Lee, Y., Gomez, E., Gosztola, D., Schaller, R.D. and Verduzco, R., Adv. Funct. Mater., 2015, 25:5578 doi: 10.1002/adfm.201502623
31. [31]
  Nakabayashi, K. and Mori, H., Macromolecules, 2012, 45:9618 doi: 10.1021/ma302170e
32. [32]
  Lin, Y.H., Smith, K.A., Kempf, C.N. and Verduzco, R., Polym. Chem., 2013, 4:229 doi: 10.1039/C2PY20830J
33. [33]
  Bu, L.J., Guo, X.Y., Yu, B., Qu, Y., Xie, Z.Y., Yan, D.H., Geng, Y.H. and Wang, F.S., J. Am. Chem. Soc., 2009, 131:13242 doi: 10.1021/ja905980w
34. [34]
  Gao, D., Hollinger, J. and Seferos, D.S., ACS Nano, 2012, 6:7114 doi: 10.1021/nn3021844
35. [35]
  Kozycz, L.M., Gao, D., Hollinger, J. and Seferos, D.S., Macromolecules, 2012, 45:5823 doi: 10.1021/ma3009349
36. [36]
  Hollinger, J., Sun, J., Gao, D., Karl, D. and Seferos, D.S., Macromol. Rapid Commun., 2013, 34:437 doi: 10.1002/marc.v34.5
37. [37]
  Chi, C., Chen, M., Liaw, D., Wu, H., Huang, Y. and Tai, Y., ACS Appl. Mater. Inter., 2014, 6:12119 doi: 10.1021/am501209t
38. [38]
  Qu, J.F., Gao, B.R., Tian, H.K., Zhang, X.J., Wang, Y., Xie, Z.Y., Wang, H.Y., Geng, Y.H. and Wang, F.S., J. Mater. Chem. A, 2014, 2:3632 doi: 10.1039/c3ta14701k
39. [39]
  Lombeck, F., Komber, H., Sepe, A.R., Friend, H. and Sommer, M., Macromolecules, 2015, 48:7851 doi: 10.1021/acs.macromol.5b01845
40. [40]
  Salleo, A., Kline, R.J., DeLongchamp, D.M. and Chabinyc, M.L., Adv. Mater., 2010, 22:3812 doi: 10.1002/adma.200903712
41. [41]
  Sirringhaus, H., Tessler, N. and Friend, R.H., Science, 1998, 280:1741. doi: 10.1126/science.280.5370.1741
42. [42]
  Duong, D.T., Phan, H., Hanifi, D., Jo, P.S., Nguyen, T.Q. and Salleo, A., Adv. Mater., 2014, 26:6069 doi: 10.1002/adma.201402015
43. [43]
  Blouin, N., Michaud, A. and Leclerc, M., Adv. Mater., 2007, 19:2295 doi: 10.1002/(ISSN)1521-4095
44. [44]
  He, Z., Zhong, C., Huang, X., Wong, W.Y., Wu, H., Chen, L., Su, S. and Cao, Y., Adv. Mater., 2011, 23:4636 doi: 10.1002/adma.201103006
45. [45]
  Ashraf, R.S., Schroeder, B.C., Bronstein, H.A., Huang, Z., Thomas, S., Kline, R.J., Brabec, C.J., Rannou, P., Anthopoulos, T.D., Durrant, J.R. and McCulloch, I., Adv. Mater., 2013, 25:2029 doi: 10.1002/adma.201300027
46. [46]
  Verswyvel, M., Steverlynck, J., Hadj Mohamed, S., Trabelsi, M., Champagne, B. and Koeckelberghs, G., Macromolecules, 2014, 47:4668 doi: 10.1021/ma500610p
47. [47]
  Dhibi, O., Ltaief, A. and Bouazizi, A., Mater. Sci. Semicond. Process., 2014, 25:173 doi: 10.1016/j.mssp.2013.11.004
48. [48]
  Guo, Y., Jiang, L., Ma, X., Hu, W. and Su, Z., Polym. Chem., 2013, 4:4308 doi: 10.1039/c3py00728f
49. [49]
  Verduzco, R., Botiz, I., Pickel, D.L., Kilbey, S.M., Hong, K., Dimasi, E. and Darling, S.B., Macromolecules, 2011, 44:530 doi: 10.1021/ma102728z
1. [1]
  Zhao Lu , Hu Lv , Qinzhuang Liu , Zhongliao Wang . Modulating NH₂ Lewis Basicity in CTF-NH₂ through Donor-Acceptor Groups for Optimizing Photocatalytic Water Splitting. Acta Physico-Chimica Sinica, 2024, 40(12): 2405005-. doi: 10.3866/PKU.WHXB202405005
2. [2]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
3. [3]
  Jiawei Li , Cheng Chen , Mingyan Wu . Donor-acceptor type organic cocrystals for deep-red circularly polarized luminescence and two-photon excited emission. Chinese Journal of Structural Chemistry, 2025, 44(3): 100513-100513. doi: 10.1016/j.cjsc.2025.100513
4. [4]
  Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2024.100463
5. [5]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
6. [6]
  Wenya Jiang , Jianyu Wei , Kuan-Guan Liu . Atomically precise superatomic silver nanoclusters stabilized by O-donor ligands. Chinese Journal of Structural Chemistry, 2024, 43(9): 100371-100371. doi: 10.1016/j.cjsc.2024.100371
7. [7]
  Chengcheng Xie , Chengyi Xiao , Hongshuo Niu , Guitao Feng , Weiwei Li . Mesoporous organic solar cells. Chinese Chemical Letters, 2024, 35(11): 109849-. doi: 10.1016/j.cclet.2024.109849
8. [8]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
9. [9]
  Kai Han , Guohui Dong , Ishaaq Saeed , Tingting Dong , Chenyang Xiao . Boosting bulk charge transport of CuWO4 photoanodes via Cs doping for solar water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100207-100207. doi: 10.1016/j.cjsc.2023.100207
10. [10]
  Yaohua Li , Qi Cao , Xuanhua Li . Tailoring the configuration of polymer passivators in perovskite solar cells. Chinese Journal of Structural Chemistry, 2025, 44(2): 100413-100413. doi: 10.1016/j.cjsc.2024.100413
11. [11]
  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
12. [12]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
13. [13]
  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
14. [14]
  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
15. [15]
  Xue Zhao , Rui Zhao , Qian Liu , Henghui Chen , Jing Wang , Yongfeng Hu , Yan Li , Qiuming Peng , John S Tse . A p-d block synergistic effect enables robust electrocatalytic oxygen evolution. Chinese Chemical Letters, 2024, 35(11): 109496-. doi: 10.1016/j.cclet.2024.109496
16. [16]
  Yiwen Lin , Yijie Chen , Chunhui Deng , Nianrong Sun . Integration of resol/block-copolymer carbonization and machine learning: A convenient approach for precise monitoring of glycan-associated disorders. Chinese Chemical Letters, 2024, 35(12): 109813-. doi: 10.1016/j.cclet.2024.109813
17. [17]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
18. [18]
  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
19. [19]
  Bo Yang , Pu-An Lin , Tingwei Zhou , Xiaojia Zheng , Bing Cai , Wen-Hua Zhang . Facile surface regulation for highly efficient and thermally stable perovskite solar cells via chlormequat chloride. Chinese Chemical Letters, 2024, 35(10): 109425-. doi: 10.1016/j.cclet.2023.109425
20. [20]
  Yingfen Li , Zhiqi Wang , Yunhai Zhao , Dajun Luo , Xueliang Zhang , Jun Zhao , Zhenghua Su , Shuo Chen , Guangxing Liang . Potassium doping for grain boundary passivation and defect suppression enables highly-efficient kesterite solar cells. Chinese Chemical Letters, 2024, 35(11): 109468-. doi: 10.1016/j.cclet.2023.109468

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(887)
HTML views(54)

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