Regulation of High Miscibility for Efficient Charge-Transport in n-Doped Conjugated Polymers
Qi-Yi Li
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorZe-Fan Yao
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorHao-Tian Wu
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorLongfei Luo
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorYi-Fan Ding
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorChi-Yuan Yang
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorXin-Yi Wang
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorZhihao Shen
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorJie-Yu Wang
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jian Pei
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorQi-Yi Li
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorZe-Fan Yao
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
These authors contributed equally to this work.
Search for more papers by this authorHao-Tian Wu
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorLongfei Luo
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorYi-Fan Ding
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorChi-Yuan Yang
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorXin-Yi Wang
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorZhihao Shen
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorJie-Yu Wang
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorCorresponding Author
Jian Pei
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871 China
Search for more papers by this authorAbstract
Strong interchain interactions of conjugated polymers usually result in poor miscibility with molecular dopants, limiting the doping efficiency because of uncontrolled phase separation. We have developed a strategy to achieve efficient charge-transport and high doping miscibility in n-doped conjugated polymers. We solve the miscibility issue through disorder side-chains containing dopants better. Systemic structural characterization reveals a farther side-chain branching point will lead to higher disorders, which provides appropriate sites to accommodate extrinsic molecular dopants without harming original chain packings and charge-transport channels. Therefore, better sustainability of solid-state microstructure is obtained, yielding a stable conductivity even when overloading massive dopants. This work highlights the importance of realizing high host-dopant miscibility in molecular doping of conjugated polymers.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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References
- 1B. Lüssem, C.-M. Keum, D. Kasemann, B. Naab, Z. Bao, K. Leo, Chem. Rev. 2016, 116, 13714.
- 2Y. Xu, H. Sun, A. Liu, H.-H. Zhu, W. Li, Y.-F. Lin, Y.-Y. Noh, Adv. Mater. 2018, 30, 1801830.
- 3V. A. Kolesov, C. Fuentes-Hernandez, W.-F. Chou, N. Aizawa, F. A. Larrain, M. Wang, A. Perrotta, S. Choi, S. Graham, G. C. Bazan, T.-Q. Nguyen, S. R. Marder, B. Kippelen, Nat. Mater. 2017, 16, 474.
- 4B. Russ, A. Glaudell, J. J. Urban, M. L. Chabinyc, R. A. Segalman, Nat. Rev. Mater. 2016, 1, 16050.
- 5K. Xu, H. Sun, T.-P. Ruoko, G. Wang, R. Kroon, N. B. Kolhe, Y. Puttisong, X. Liu, D. Fazzi, K. Shibata, C.-Y. Yang, N. Sun, G. Persson, A. B. Yankovich, E. Olsson, H. Yoshida, W. M. Chen, M. Fahlman, M. Kemerink, S. A. Jenekhe, C. Müller, M. Berggren, S. Fabiano, Nat. Mater. 2020, 19, 738.
- 6W. Zhao, J. Ding, Y. Zou, C. Di, D. Zhu, Chem. Soc. Rev. 2020, 49, 7210.
- 7G. Kim, L. Shao, K. Zhang, K. P. Pipe, Nat. Mater. 2013, 12, 719.
- 8K. A. Peterson, E. M. Thomas, M. L. Chabinyc, Annu. Rev. Mater. Res. 2020, 50, 551.
- 9Y. Lu, J.-Y. Wang, J. Pei, Chem. Mater. 2019, 31, 6412.
- 10S. Wang, H. Sun, U. Ail, M. Vagin, P. O. Å Persson, J. W. Andreasen, W. Thiel, M. Berggren, X. Crispin, D. Fazzi, S. Fabiano, Adv. Mater. 2016, 28, 10764.
- 11J. Liu, G. Ye, B. Zee, J. Dong, X. Qiu, Y. Liu, G. Portale, R. Chiechi, L. Koster, Adv. Mater. 2018, 30, 1804290.
- 12V. Vijayakumar, Y. Zhong, V. Untilova, M. Bahri, L. Herrmann, L. Biniek, N. Leclerc, M. Brinkmann, Adv. Energy Mater. 2019, 9, 1900266.
- 13Y. Lu, Z.-D. Yu, H.-I. Un, Z.-F. Yao, H.-Y. You, W. Jin, L. Li, Z.-Y. Wang, B.-W. Dong, S. Barlow, E. Longhi, C. Di, D. Zhu, J.-Y. Wang, C. Silva, S. R. Marder, J. Pei, Adv. Mater. 2021, 33, 2005946.
- 14C. Zhang, X. Zhu, Adv. Funct. Mater. 2020, 30, 2000765.
- 15K. Shi, F. Zhang, C.-A. Di, T.-W. Yan, Y. Zou, X. Zhou, D. Zhu, J.-Y. Wang, J. Pei, J. Am. Chem. Soc. 2015, 137, 6979.
- 16Y. Lu, Z. Di Yu, R. Z. Zhang, Z. F. Yao, H. Y. You, L. Jiang, H. I. Un, B. W. Dong, M. Xiong, J. Y. Wang, J. Pei, Angew. Chem. Int. Ed. 2019, 58, 11390; Angew. Chem. 2019, 131, 11512.
- 17R. A. Schlitz, F. G. Brunetti, A. M. Glaudell, P. L. Miller, M. A. Brady, C. J. Takacs, C. J. Hawker, M. L. Chabinyc, Adv. Mater. 2014, 26, 2825.
- 18J. Liu, L. Qiu, R. Alessandri, X. Qiu, G. Portale, J. Dong, W. Talsma, G. Ye, A. A. Sengrian, P. C. T. Souza, M. A. Loi, R. C. Chiechi, S. J. Marrink, J. C. Hummelen, L. J. A. Koster, Adv. Mater. 2018, 30, 1704630.
- 19Y. Lu, Z.-D. Yu, Y. Liu, Y.-F. Ding, C.-Y. Yang, Z.-F. Yao, Z.-Y. Wang, H.-Y. You, X.-F. Cheng, B. Tang, J.-Y. Wang, J. Pei, J. Am. Chem. Soc. 2020, 142, 15340.
- 20J. E. Cochran, M. J. N. Junk, A. M. Glaudell, P. L. Miller, J. S. Cowart, M. F. Toney, C. J. Hawker, B. F. Chmelka, M. L. Chabinyc, Macromolecules 2014, 47, 6836.
- 21R. Kroon, D. Kiefer, D. Stegerer, L. Yu, M. Sommer, C. Müller, Adv. Mater. 2017, 29, 1700930.
- 22L. Ye, H. Hu, M. Ghasemi, T. Wang, B. A. Collins, J.-H. Kim, K. Jiang, J. H. Carpenter, H. Li, Z. Li, T. McAfee, J. Zhao, X. Chen, J. L. Y. Lai, T. Ma, J.-L. Bredas, H. Yan, H. Ade, Nat. Mater. 2018, 17, 253.
- 23T. Wang, J.-L. Brédas, J. L. Bredas, J.-L. Brédas, J. L. Bredas, J. Am. Chem. Soc. 2021, 143, 1822.
- 24Q.-Y. Li, Z.-F. Yao, J.-Y. Wang, J. Pei, Rep. Prog. Phys. 2021, 84, 076601.
- 25A. M. Glaudell, J. E. Cochran, S. N. Patel, M. L. Chabinyc, Adv. Energy Mater. 2015, 5, 1401072.
- 26E. E. Perry, C.-Y. Chiu, K. Moudgil, R. A. Schlitz, C. J. Takacs, K. A. O'Hara, J. G. Labram, A. M. Glaudell, J. B. Sherman, S. Barlow, Chem. Mater. 2017, 29, 9742.
- 27Y. Shin, M. Massetti, H. Komber, T. Biskup, D. Nava, G. Lanzani, M. Caironi, M. Sommer, Adv. Electron. Mater. 2018, 4, 1700581.
- 28J. Liu, G. Ye, H. G. O. Potgieser, M. Koopmans, S. Sami, M. I. Nugraha, D. R. Villalva, H. Sun, J. Dong, X. Yang, X. Qiu, C. Yao, G. Portale, S. Fabiano, T. D. Anthopoulos, D. Baran, R. W. A. Havenith, R. C. Chiechi, L. J. A. Koster, Adv. Mater. 2021, 33, 2006694.
- 29Y.-Q. Zheng, Z. Yao, J. Dou, Y. Wang, W. Ma, L. Zou, S. Nikzad, Q.-Y. Li, Z.-H. Sun, Z. Yu, W.-B. Zhang, J. Wang, J. Pei, Giant 2021, 7, 100064.
- 30Z.-F. Yao, J.-Y. Wang, J. Pei, Chem. Sci. 2021, 12, 1193.
- 31C.-Y. Yang, Y.-F. Ding, D. Huang, J. Wang, Z.-F. Yao, C.-X. Huang, Y. Lu, H.-I. Un, F.-D. Zhuang, J.-H. Dou, C. Di, D. Zhu, J.-Y. Wang, T. Lei, J. Pei, Nat. Commun. 2020, 11, 3292.
- 32J. Mei, D. Hwan Kim, A. L. Ayzner, M. F. Toney, Z. Bao, D. H. H. Kim, A. L. L. Ayzner, M. F. F. Toney, Z. Bao, J. Am. Chem. Soc. 2011, 133, 20130.
- 33Y. Wang, K. Takimiya, Adv. Mater. 2020, 32, 2002060.
- 34Z. Wu, A. Petzold, T. Henze, T. Thurn-Albrecht, R. H. Lohwasser, M. Sommer, M. Thelakkat, Macromolecules 2010, 43, 4646.
- 35Y. Yuan, J. Zhang, J. Sun, J. Hu, T. Zhang, Y. Duan, Macromolecules 2011, 44, 9341.
- 36Y.-F. Yao, R. Graf, H. W. Spiess, S. Rastogi, Macromolecules 2008, 41, 2514.
- 37R. Born, H. W. Spiess, Macromolecules 1995, 28, 7785.
- 38A. Melnyk, M. J. N. Junk, M. D. McGehee, B. F. Chmelka, M. R. Hansen, D. Andrienko, J. Phys. Chem. Lett. 2017, 8, 4155.
- 39G. Han, Y. Yi, Z. Shuai, Adv. Energy Mater. 2018, 8, 1702743.
- 40K. Do, M. K. Ravva, T. Wang, J.-L. Brédas, Chem. Mater. 2017, 29, 346.
- 41Z. Yao, Y. Zheng, J. Dou, Y. Lu, Y. Ding, L. Ding, J. Wang, J. Pei, Adv. Mater. 2021, 33, 2006794.
- 42J. Gao, J. D. Roehling, Y. Li, H. Guo, A. J. Moulé, J. K. Grey, J. Mater. Chem. C 2013, 1, 5638.
- 43N. I. Craciun, J. Wildeman, P. W. M. Blom, Phys. Rev. Lett. 2008, 100, 1.
- 44S. Schott, E. Gann, L. Thomsen, S.-H. Jung, J.-K. Lee, C. R. McNeill, H. Sirringhaus, Adv. Mater. 2015, 27, 7356.
- 45A. Liang, X. Zhou, W. Zhou, T. Wan, L. Wang, C. Pan, L. Wang, Macromol. Rapid Commun. 2017, 38, 1600817.
- 46C.-K. Mai, R. A. Schlitz, G. M. Su, D. Spitzer, X. Wang, S. L. Fronk, D. G. Cahill, M. L. Chabinyc, G. C. Bazan, J. Am. Chem. Soc. 2014, 136, 13478.
- 47A. Yildiz, N. Serin, T. Serin, M. Kasap, Jpn. J. Appl. Phys. 2009, 48, 111203.
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