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2020 , Vol. 40 >Issue 4: 831 - 855

DOI: https://doi.org/10.6023/cjoc201910042

综述与进展

C—H键直接芳基化制备共轭功能材料及其器件应用

  • 刘慧 ,
  • 张小凤 ,
  • 程敬招 ,
  • 叶东鼐 ,
  • 陈龙 ,
  • 温和瑞 ,
  • 刘诗咏
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  • a 江西理工大学材料冶金化学学部 江西赣州 341000;
    b 天津大学化学系 天津 300072

收稿日期: 2019-10-31

  修回日期: 2019-11-29

  网络出版日期: 2019-12-27

基金资助

国家自然科学基金（No.21374075）资助项目.

收起

Direct C—H Arylation-Derived π-Conjugated Functional Materials for Device Applications

  • Liu Hui ,
  • Zhang Xiaofeng ,
  • Cheng Jingzhao ,
  • Ye Dongnai ,
  • Chen Long ,
  • Wen Herui ,
  • Liu Shiyong
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  • a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou Jiangxi 341000;
    b Department of Chemistry, Tianjin University, Tianjin 300072

Received date: 2019-10-31

  Revised date: 2019-11-29

  Online published: 2019-12-27

Supported by

Project supported by the National Natural Science Foundation of China (No. 21374075).

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摘要

π-共轭光电聚合物及小分子，由于其成本低、质量轻、可溶液加工性以及结构与性能的丰富可调控性，已成为新一代光电功能器件重要的半导体材料.C—B/C—X及C—Sn/C—X键Suzuki及Stille偶联是有机半导体材料中sp2-C—C键最常用的构建策略.然而，传统的C—C键偶联需要对反应底物进行预官能团化，合成步骤繁琐，且伴随有毒副产物的生成.直接芳基化反应利用C—H/C—X键偶联构建sp2-C—C键，反应底物不涉及有机金属试剂，具有良好的原子及步骤经济性，在有机光电材料的高效合成及实际应用领域拥有巨大的潜力，因而成为人们关注的焦点.针对直接芳基化法制备有机共轭功能材料的器件应用研究进行了总结综述，分别就有机太阳能电池、场效应晶体管、染料敏化和钙钛矿电池、有机发光二极管及锂电池进行分类讨论，系统介绍了该领域的研究进展，并对今后发展进行了展望.

关键词： C—H键直接芳基化; 共轭功能材料; 原子及步骤经济性; 有机太阳能电池; 有机场效应晶体管; 有机光电器件

本文引用格式

刘慧 , 张小凤 , 程敬招 , 叶东鼐 , 陈龙 , 温和瑞 , 刘诗咏 . C—H键直接芳基化制备共轭功能材料及其器件应用[J]. 有机化学, 2020 , 40(4) : 831 -855 . DOI: 10.6023/cjoc201910042

Abstract

Organic π-conjugated polymers and small molecules, featured by low cost, light weight, solution processibility as well as finely adjustable structure and properties, have become kinds of fundamental semiconductor materials for next generation of optoelectric devices. The C——B/C——X Suzuki and C——Sn/C——X Stille couplings have become the most widely used strategy for the construction of sp2-C——C bonds involved in organic semiconductor materials. However, these traditional C——C coupling reactions usually involve prefunctionalization of subtrates and multipe synthetic steps, along with toxic by-products. In recent years, the direct C——H arylation reaction (C——H/C——X coupling) for the construction of sp2-C——C bonds and the synthesis of organic π-conjugated materials, featured by the simplicity without use of organometallic precursors, high atom- and step-econogy and low cost, has attracted extensive attention from researchers, due to its great potential for pratical applictions. The C——H/C——X direct arylation coupling has great potential in the efficient synthesis and practical application of organic optoelectric materials. Herein, an overview of recent developments in direct C——H arylation for the synthesis of organic conjugated functional materials used in device applications is provided, including organic photovoltaics (OPV), organic field effect transistor (OFET), dye-sensitized solar cell (DSSC), perovskite cells (PSC), organic light emitting diode (OLED) and lithium rattery, etc. The advantages, challenges as well as the future developments in the area of direct C——H arylation are also discussed and commented.

Key words： direct C—H arylation; π-conjugated functional materials; atom- and step-economic synthesis; organic solar cells; organic field effect transitors; organic optoelectric devices

参考文献

[1] Chiang, C. K.; Fincher, C. R. J.; Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Macdiarmid, A. G. Phys. Rev. Lett. 1977, 39, 1098.
[2] Chiang, C. K.; Druy, M. A.; Gau, S. C.; Heeger, A. J.; Louis, E. J.; MacDiarmid, A. G.; Park, Y. W.; Shirakawa, H. J. Am. Chem. Soc. 1978, 100, 1013.
[3] Yu, S.; Peng, A.; Zhang, S.; Huang, H. Sci. China Chem. 2018, 61, 1359.
[4] Di, B.-H.; Chen, Y.-L. Chin. Chem. Lett. 2018, 29, 245.
[5] Chen, X.; He, Y.; Ali, M. U.; He, Y.; Zhu, Y.; Li, A.; Zhao, C.; Perepichka, I. F.; Meng, H. Sci. China Chem. 2019, 62, 1360.
[6] Yang, L.; Yin, C.-Z.; Ali, M. A.; Dong, C.-Y.; Xie, X.-M.; Wu, X.-P.; Wang, Y.-X.; Yu, Y.; Xie, L.-H.; Bian, L.-Y.; Bao, J.-M.; Ran, X.-Q.; Huang, W. Chin. J. Chem. 2019, 37, 915.
[7] Songbuer; Li, M.; Imerhasan, M. Chin. J. Org. Chem. 2018, 38, 594(in Chinese). (松布尔, 李明辉, 穆赫塔尔·伊米尔艾山, 有机化学, 2018, 38, 594.)
[8] He, P.; Zhang, H.; Xu, C.; Zhen, Y.; Dong, H.; Hu, W. Chin. Chem. Lett. 2019, 30, 903.
[9] Song, X.; Zhao, J.; Zhang, W.; Chen, L. Chin. Chem. Lett. 2018, 29, 331.
[10] Ostroverkhova, O. Chem. Rev. 2016, 116, 13279.
[11] Gather, M. C.; Kohnen, A.; Meerholz, K. Adv. Mater. 2011, 23, 233.
[12] Xiao, L.; Chen, Z.; Qu, B.; Luo, J.; Kong, S.; Gong, Q.; Kido, J. Adv. Mater. 2011, 23, 926.
[13] Xu, R.-P.; Li, Y.-Q.; Tang, J.-X. J. Mater. Chem. C 2016, 4, 9116.
[14] Facchetti, A. Chem. Mater. 2011, 23, 733.
[15] Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. J. Am. Chem. Soc. 2013, 135, 6724.
[16] Sirringhaus, H. Adv. Mater. 2014, 26, 1319.
[17] Kan, J.; Wang, S.; Wang, Z.; Guo, S.; Wang, W.; Li, L. Chin. Chem. Lett. 2018, 29, 1681.
[18] Zhang, C.; Zhang, F.; Ding, L.; Ni, Z.; Jiang, L.; Dong, H.; Zhang, X.; Li, R.; Hu, W. Chem. J. Chin. Univ. 2018, 39, 102(in Chinese). (张婵婵, 张方辉, 丁磊, 倪振杰, 江浪, 董焕丽, 张小涛, 李荣金, 胡文平, 高等学校化学学报, 2018, 39, 102.)
[19] Li, J.; Hu, Y.-H.; Ge, C.-W.; Gong, H.-G.; Gao, X.-K. Chin. Chem. Lett. 2018, 29, 423.
[20] Fu, L.-N.; Leng, B.; Li, Y.-S.; Gao, X.-K. Chin. Chem. Lett. 2018, 29, 175.
[21] Bian, L.; Zhu, E.; Tang, J.; Tang, W.; Zhang, F. Prog. Polym. Sci. 2012, 37, 1292.
[22] Kang, H.; Lee, W.; Oh, J.; Kim, T.; Lee, C.; Kim, B. J. Acc. Chem. Res. 2016, 49, 2424.
[23] Jin, Y.; Chen, Z.; Dong, S.; Zheng, N.; Ying, L.; Jiang, X. F.; Liu, F.; Huang, F.; Cao, Y. Adv. Mater. 2016, 28, 9811.
[24] Zhang, Y.; Yao, H.; Zhang, S.; Qin, Y.; Zhang, J.; Yang, L.; Li, W.; Wei, Z.; Gao, F.; Hou, J. Sci. China Chem. 2018, 61, 1328.
[25] Lin, J.-D.; Zhong, L.; Wu, F.-P.; Li, Y.; Yuan, Y.; Bin, H.; Zhang, Z.; Liu, F.; Fan, J.; Zhang, Z.-G.; Liao, L.-S.; Jiang, Z.-Q.; Li, Y. Sci. China Chem. 2018, 61, 1405.
[26] Fan, Q.; Su, W.; Wang, Y.; Guo, B.; Jiang, Y.; Guo, X.; Liu, F.; Russell, T. P.; Zhang, M.; Li, Y. Sci. China Chem. 2018, 61, 531.
[27] Su'ait, M. S.; Rahman, M. Y. A.; Ahmad, A. Sol. Energy 2015, 115, 452.
[28] Yuna, S.; Freitas, J. N.; Nogueirac, A. F; Wang, Y.; Ahmade, S.; Wang, Z.-S. Prog. Polym. Sci. 2016, 59, 1.
[29] Chang, Y.-C.; Lee, K.-M.; Lai, C.-H.; Liu, C.-Y. Chem. Asian J. 2018, 13, 1510.
[30] Magliulo, M.; Manoli, K.; Macchia, E.; Palazzo, G.; Torsi, L. Adv. Mater. 2015, 27, 7528.
[31] Zhang, C.; Chen, P.; Hu, W. Chem. Soc. Rev. 2015, 44, 2087.
[32] Zhou, X.; Cheng, X.; Zhu, Y.; Elzatahryc, A. A.; Alghamdie, A.; Denga, Y.; Zhao, D. Chin. Chem. Lett. 2018, 29, 405.
[33] (a) Hu, Z.; Ying, L.; Huang, F.; Cao, Y. Sci. China Chem. 2017, 60, 571.
(b) Berny, S.; Blouin, N.; Distler, A.; Egelhaaf, H.-J.; Krompiec, M.; Lohr, A.; Lozman, O. R.; Morse, G. E.; Nanson, L.; Pron, A.; Tierney, S.; Tiwana, P.; Wagner, M.; Wilson, H. Adv. Sci. 2016, 3, 1500342.
(c) Cheng, P.; Zhan, X. Chem. Soc. Rev. 2016, 45, 2544.
[34] (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
(b) Bergman, R. G. Nature 2007, 446, 391.
[35] Tang, R.-Y.; Li, G.; Yu, J.-Q. Nature 2014, 507, 215.
[36] Davies, H. M. L.; Morton, D. J. Org. Chem. 2016, 81, 343.
[37] Wang, Y.; Yu, X.; Fu, H.; Zheng, X.; Chen, H.; Li, R. Chin. J. Org. Chem. 2019, 39, 482(in Chinese). (汪洋点点, 余晓军, 付海燕, 郑学丽, 陈华, 李瑞祥, 有机化学, 2019, 39, 482.)
[38] Pierpont, C. G.; Mazza, M. C. Inorg. Chem. 1974, 13, 8.
[39] Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Ofele, K.; Beller, M. Chem. Eur. J. 1997, 3, 8.
[40] (a) Corwin, A. H.; Naylor, M. A. J. Am. Chem. Soc. 1947, 69, 1004.
(b) Klapproth, W. L.; Westheimer, F. H. J. Am. Chem. Soc. 1950, 72, 4461.
[41] (a) Lapointe, D.; Fagnou K. Chem. Lett. 2010, 39, 1118.
(b) Ackermann, L. Chem. Rev. 2011, 111, 1315.
[42] Rudenko, A. E.; Thompson, B. C. Polym. Chem. 2015, 53, 135.
[43] Suraru, S.-L.; Lee, J. A.; Luscombe, C. K. ACS Macro Lett. 2016, 5, 724.
[44] Gobalasingham, N. S.; Thompson, B. C. Prog. Polym. Sci. 2018, 83, 135.
[45] Kuwabara, J.; Kanbara, T. J. Synth. Org. Chem. 2014, 72, 1271.
[46] Kowalski, S.; Allard, S.; Zilberberg, K.; Riedl, T.; Scherf, U. Prog. Polym. Sci. 2013, 38, 1805.
[47] Mercier, L. G.; Leclerc, M. Acc. Chem. Res. 2013, 46, 1597.
[48] Wang, K.; Wang, M. F. Curr. Org. Chem. 2013, 17, 1001.
[49] Bura, T.; Blaskovits, J. T.; Leclerc, M. J. Am. Chem. Soc. 2016, 138, 10056.
[50] Yu, S.; Liu, F. C.; Yu, J. W.; Zhang, S. M.; Cabanetos, C.; Gao, Y. Q.; Huang, W. J. Mater. Chem. C 2017, 5, 29.
[51] Wu, W. T.; Xin, H. S.; Ge, C. W.; Gao, X. K. Tetrahedron Lett. 2017, 58, 175.
[52] Bohra, H.; Wang, M. F. J. Mater. Chem. A 2017, 5, 11550.
[53] Okamoto, K.; Zhang, J. X.; Housekeeper, J. B.; Marder, S. R.; Luscombe, C. K. Macromolecules 2013, 46, 8059.
[54] Zhang, Q.; Chang, M. J.; Lu, Y.; Sun, Y. N.; Li, C. X.; Yang, X. L.; Zhang, M. T.; Chen, Y. S. Macromolecules 2018, 51, 379.
[55] Kuwabara, J. P. Polym. J. 2018, 50, 1099.
[56] Geng, Y. H.; Sui, Y. Acta Polym. Sin. 2019, 50, 109(in Chinese). (耿延候, 睢颖, 高分子学报, 2019, 50, 109.)
[57] Sevignon, M.; Papillon, J.; Schulz, E.; Lemaire, M. Tetrahedron Lett. 1999, 40, 5873.
[58] Wang, Q.; Takita, R.; Kikuzaki, Y.; Ozawa F. J. Am. Chem. Soc. 2010, 132, 11420.
[59] Ni, Z.; Wang, H.; Dong, H.; Dang, Y.; Zhao, Q.; Zhang, X.; Hu, W. Nat. Chem. 2019, 271.
[60] Wen, Z.; Ma, X.; Yang, X.; Bi, P.; Niu, M.; Zhang, K.; Feng, L.; Hao, X. Chin. Chem. Lett. 2019, 30, 995.
[61] Jo, J.; Pron, A.; Berrouard, P.; Leong, W. L.; Yuen, J. D.; Moon, J. S.; Leclerc, M.; Heeger, A. J. Adv. Energy Mater. 2012, 2, 1397.
[62] Mercier, L. G.; Aich, B. R.; Najari, A.; Beaupre, S.; Berrouard, P.; Pron, A.; Robitaille, A.; Taob, Y.; Leclerc, M. Polym. Chem. 2013, 4, 5252.
[63] Wang, D. H.; Pron, A.; Leclerc, M.; Heeger, A. J. Adv. Funct. Mater. 2013, 23, 1297.
[64] Kuwabara, J.; Fujie, Y.; Maruyama, K.; Yasuda, T.; Kanbara, T. Macromolecules 2016, 49, 9388.
[65] Dudnik, A. S.; Aldrich, T. J.; Eastham, N. D.; Chang, R. P. H.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2016, 138, 15699.
[66] Xin, H.; Ge, C.; Jiao, X.; Yang, X.; Rundel, K.; McNeill, C.; Gao, X. Angew. Chem., Int. Ed. 2017, 57, 1322.
[67] Welsh, T. A.; Laventure, A.; Welch, G. C. Molecules 2018, 23, 931.
[68] Wienk, M. M.; Turbiez, M.; Gilot, J.; Janssen, R. A. Adv. Mater. 2008, 20, 2556.
[69] Tamayo, A. B.; Tantiwiwat, M.; Walker, B.; Nguyen, T.-Q. J. Phys. Chem. C 2008, 112, 15543.
[70] Zhang, J.; Kang, D. Y.; Barlow, S.; Marder, S. R. J. Mater. Chem. 2012, 22, 21392.
[71] Liu, S. Y.; Shi, M. M.; Huang, J. C.; Jin, J. N.; Hu, X. L.; Pan, J. Y.; Li, H. Y.; Jen, A. K. Y.; Chen, H. Z. J. Mater. Chem. A 2013, 1, 2795.
[72] Liu, S.-Y.; Fu, W.-F.; Xu, J.-Q.; Fan, C.-C.; Jiang, H.; Shi, M.; Li, H.-Y.; Chen, J.-W.; Cao, Y.; Chen, H.-Z. Nanotechnology 2014, 25, 014006.
[73] Liu, S.-Y.; Liu, W.-Q.; Xu, J.-Q.; Fan, C.-C.; Fu, W.-F.; Ling, J.; Wu, J.-Y.; Shi, M.-M.; Jen, A. K.-Y.; Chen, H.-Z. ACS Appl. Mater. Interfaces 2014, 6, 6765.
[74] Liu, S.-Y.; Jung, J. W.; Li, C.-Z.; Huang, J.; Zhang, J.; Chen, H. Z.; Jen, A. K.-Y. J. Mater. Chem. A 2015, 3, 22162.
[75] Liu, S.-Y.; Liu, W.-Q.; Yuan, C.-X.; Zhong, A.-G.; Han, D.; Wang, B.; Shah, M. N.; Shi, M.-M.; Chen, H. Z. Dyes Pigm. 2016, 134, 139.
[76] Liu, S.-Y.; Wu, C.-H.; Li, C.-Z.; Liu, S.-Q.; Wei, K.-H.; Chen, H.-Z.; Jen, A. K.-Y. Adv. Sci. 2015, 1500014.
[77] Sun, M.; Wang, W.; Lv, W.; Lu, M.; Yan, S.; Liang, L.; Ling, Q. D. Synth. Met. 2015, 209, 412.
[78] Lu, M.; Wang, W.; Lv, W.; Yan, S.; Zhang, T.; Zhen, H.; Ling, Q. D. RSC Adv. 2016, 6, 86276.
[79] Homyak, P.; Liu, Y.; Liu, F.; Russel, T. P.; Coughlin, E. B. Macromolecules 2015, 48, 6978.
[80] Maglione, C.; Carella, A.; Centore, R.; Chavez, P.; Leveque, P.; Fall, S.; Leclerc, N. Dyes Pigm.2017, 141, 169.
[81] Bura, T.; Beaupré, S.; Ibraikulov, O.A.; Legaré, M.-A.; Quinn, J.; Levéque, P.; Heiser, T.; Li, Y.; Leclerc, N.; Leclerc, M. Macromolecules 2017, 50, 7080.
[82] Payne, A.-J.; Li, S.; Dayneko, S. V.; Risko, C.; Welch, G. C. Chem. Commun. 2017, 53, 10168.
[83] McAfee, S. M.; Dayneko, S. V.; Hendsbee, A. D.; Josse, P.; Blanchard, P.; Cabanetos, C.; Welch, G. C. J. Mater. Chem. A 2017, 5, 11623.
[84] Aldrich, T. J.; Dudnik, A. S.; Eastham, N. D.; Manley, E. F.; Chen, L. X.; Chang, R. P. H.; Melkonyan, F. S.; Facchetti, A.; Marks, T. J. Macromolecules 2018, 51, 9140.
[85] Kuwabara, J.; Yasuda, T.; Choi, S. J.; Lu, W.; Yamazaki, K.; Kagaya, S.; Han, L.; Kanbara, T. Adv. Funct. Mater. 2014, 24, 3226.
[86] Kuwabara, J.; Takase, N.; Yasuda, T.; Kanbara, T. Polym. Chem. 2016, 54, 2337.
[87] Elsawy, W.; Kang, H.; Yu, K.; Elbarbary, A.; Lee, K.; Lee, J.-S. Polym. Chem.2014, 52, 2926.
[88] Shaker, M.; Trinh, C. K.; Kim, W.; Kim, H.; Lee, K.; Lee, J.-S. New J. Chem. 2015, 39, 4957.
[89] Grenier, F.; Aïch, B. R.; Lai, Y.-Y.; Guérette, M.; Holmes, A. B.; Tao, Y.; Wong, W. W. H.; Leclerc, M. Chem. Mater. 2015, 27, 2137.
[90] Chang, S.-W.; Waters, H.; Kettle, J.; Kuo, Z.-R.; Li, C.-H.; Yu, C.-Y.; Horie, M. Macromol. Rapid Commun. 2012, 33, 1927.
[91] Chang, S.-W.; Waters, H.; Kettle, J.; Horie, M. Org. Electron. 2012, 13, 2967.
[92] Sharma, B.; Singh, A.; Afroz, M. A.; Iyer, P. K.; Jacob, J. Synth. Met. 2017, 226, 56.
[93] Gobalasingham, N. S.; Ekiz, S.; Pankow, R. M.; Livi, F.; Bundgaard, E.; Thompson, B. C. Polym. Chem. 2017, 8, 4393.
[94] Wang, K.; Chen, H.; Wei, X.; Bohra, H.; He, F.; Wang, M. Dyes Pigm. 2018, 158, 183.
[95] Marzano, G.; Kotowski, D.; Babudri, F.; Musio, R.; Pellegrino, A.; Luzzati, S.; Po, R.; Farinola, G. M. Macromolecules 2015, 48, 7039.
[96] Chen, S.; Lee, K. C.; Zhang, Z.-G.; Kim, D. S.; Li, Y.; Yang, C. Macromolecules 2016, 49, 527.
[97] Kudrjasova, J.; Kesters, J.; Verstappen, P.; Brebels, J.; Vangerven, T.; Cardinaletti, I.; Drijkoningen, J.; Penxten, H.; Manca, J.; Lutsen, L.; Vanderzande, D.; Maes, W. J. Mater. Chem. A 2016, 4, 791.
[98] Garcias-Morales, C.; Romero-Borja, D.; Maldonado, J.-L.; Roa, A. E.; Rodríguez, M.; García-Merinos, J. P.; Ariza-Castolo, A. Molecules 2017, 22, 1607.
[99] Nakanishi, T.; Shirai, Y.; Han, L. J. Mater. Chem. A 2015, 3, 4229.
[100] Livi, F.; Gobalasingham, N. S.; Thompson, B. C.; Bundgaard, E. Polym. Chem. 2016, 54, 2907.
[101] Josse, P.; Chavez, P.; Dindault, C.; Dalinot, C.; McAfee, S. M.; Dabos-Seignon. S.; Tondelier. D.; Welch. G.; Blanchard. P.; Leclerc, N.; Cabanetos, C. Dyes Pigm. 2017, 137, 576.
[102] Hendsbee, A. D.; Dayneko, S. V.; Pells, J. A.; Cann, J. R.; Welch, G. C. Sustainable Energy Fuels 2017, 1, 1137.
[103] Welsh, T. A.; Laventure, A.; Baumgartner, T.; Welch, G. C. J. Mater. Chem. C 2018, 6, 2148.
[104] Dudnik, A. S.; Aldrich, T. J.; Eastham, N. D.; Chang, R. P. H.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2016, 138, 15699.
[105] Kang, I.; Yun, H. J.; Chung, D. S.; Kwon, S. K.; Kim, Y. H. J. Am. Chem. Soc. 2013, 135, 14896.
[106] Sonar, P.; Foonga, T. R. B.; Dodabalapur, A. Phys. Chem. Chem. Phys. 2014, 16, 4275.
[107] Hendsbee, A. D.; Sun, J.-P.; Rutledge, L. R.; Hill, I. G.; Welch, G. C. J. Mater. Chem. A 2014, 2, 4198.
[108] Pouliot, J.-R.; Sun, B.; Leduc, M.; Najari, A.; Lib, Y.; Leclerc, M. Polym. Chem. 2015, 6, 278.
[109] Shao, J.; Wang, G.; Wang, K.; Yang, C.; Wang, M. Polym. Chem. 2015, 6, 6836.
[110] Wang, K.; Wang, G.; Wang, M. Macromol. Rapid Commun. 2015, 36, 2162.
[111] Broll, S.; Nübling, F.; Luzio, A.; Lentzas, D.; Komber, H.; Caironi, M.; Sommer, M. Macromolecules 2015, 48, 7481.
[112] Lei, T.; Dou, J.-H.; Ma, Z.-J.; Yao, C.-H.; Liu, C.-J.; Wang, J.-Y.; Pei, J. J. Am. Chem. Soc. 2012, 134, 20025.
[113] Poduval, M. K.; Burrezo, P. M.; Casado, J.; Navarrete, J. T. L.; Ortiz, R. P.; Kim, T.-H. Macromolecules 2013, 46, 9220.
[114] Matsidik, R.; Komber, H.; Luzio, A.; Caironi, M.; Sommer, M. J. Am. Chem. Soc. 2015, 137, 6705.
[115] Gao, Y.; Zhang, X.; Tian, H.; Zhang, J.; Yan, D.; Geng, Y.; Wang, F. Adv. Mater. 2015, 27, 6753.
[116] Gao, Y.; Deng, Y.; Tian, H.; Zhang, J.; Yan, D.; Geng, Y.; Wang, F. Adv. Mater. 2017, 29, 1606217.
[117] Song, H.; Deng, Y.; Gao, Y.; Jiang, Y.; Tian, H.; Yan, D.; Geng, Y.; Wang, F. Macromolecules 2017, 50, 2344.
[118] Gao, Y.; Bai, J.; Sui, Y.; Han, Y.; Deng, Y.; Tian, H.; Geng, Y.; Wang, F. Macromolecules 2018, 51, 8752.
[119] Chen, F.; Jiang, Y.; Sui, Y.; Zhang, J.; Tian, H.; Han, Y.; Deng, Y.; Hu, W.; Geng, Y. Macromolecules 2018, 51, 8652.
[120] Guo, C.; Quinn, J.; Sun, B.; Li, Y. Polym. Chem. 2016, 7, 4515.
[121] Nohara, Y.; Kuwabara, J.; Yasuda, T.; Han, L.; Kanbara, T. Polym. Chem. 2014, 52, 1401.
[122] Wang, Y.; Hasegawa, T.; Matsumoto, H.; Michinobu, T. Angew. Chem., Int. Ed. 2019, 58, 2.
[123] Huang, J.; Wang, K.; Gupta, S.; Wang, G.; Yang, C.; Mushrif, S. H.; Wang, M. Polym. Chem. 2016, 54, 2015.
[124] Efrem, A.; Wang, K.; Wang, M. Dyes Pigm. 2017, 145, 331.
[125] Zhang, J. X.; Parker, T. C.; Chen, W.; Williams, L.; Khrustalev, V. N.; Jucov, E. V.; Barlow, S.; Timofeeva, T. V.; Marder, S. R. J. Org. Chem. 2016, 81, 360.
[126] Shi, Q.; Tatum, W.; Zhang, J.; Scott, C.; Luscombe, C. K.; Marder, S. R.; Blakey, S. B. Asian J. Org. Chem. 2018, 58, 10698.
[127] Wang, Y.; Zheng, L.; Li, J.; Liu, C.; Yao, J. Chin. J. Org. Chem. 2018, 38, 3143(in Chinese). (王宇飞, 郑丽萍, 李靖靖, 刘超, 姚建华, 有机化学, 2018, 38, 3143.)
[128] Lu, W.; Kuwabara, J.; Iijima, T.; Higashimura, H.; Hayashi, H.; Kanbara, T. Macromolecules 2012, 45, 4128.
[129] Aoki, H.; Saito, H.; Shimoyama, Y.; Kuwabara, J.; Yasuda, T.; Kanbara, T. ACS Macro Lett. 2018, 7, 90.
[130] Sun, M.-L.; Zhu, W.-S.; Zhang, Z.-S.; Ou, C.-J.; Xie, L.-H.; Yang, Y.; Qian, Y.; Zhao, Y.; Huang, W. J. Mater. Chem. C 2015, 3, 94.
[131] Beydoun, K.; Zaarour, M.; Williams, J. A. G.; Doucet, H.; Guerchais, V. Chem. Commun. 2012, 48, 1260.
[132] Faradhiyani, A.; Zhang, Q.; Maruyama, K.; Kuwabara, J.; Yasuda, T.; Kanbara, T. Mater. Chem. Front. 2018, 2, 1306.
[133] Li, J.; Liu, X.; Cui, P.; Li, J.; Ye, T.; Wang, X.; Zhang, C.; Zhao, Y. Sci. China Chem. 2019, 62, 1257.
[134] O'Regan, B.; Gratzel, M. Nature 1991, 353, 737.
[135] Lin, P.-H.; Lu, T.-J.; Cai, D.-J.; Lee, K.-M.; Liu, C.-Y. ChemSusChem 2015, 8, 3222.
[136] Lin, P.-H.; Liu, K.-T.; Liu, C.-Y. Chem.-Eur. J. 2015, 21, 1.
[137] Lu, K.-M.; Li, W.-M.; Lin, P.-Y.; Liu, K.-T.; Liu, C.-Y. Adv. Synth. Catal. 2017, 392, 177.
[138] Matsumura, K.; Yoshizaki, S.; Maitani, M. M.; Wada, Y.; Ogomi, Y.; Hayase, S.; Kaiho, T.; Fuse, S.; Tanaka, H.; Takahashi, T. Chem.-Eur. J. 2015, 21, 9742.
[139] Zheng, L.; Cao, Q.; Wang, J.; Chai, Z.; Cai, G.; Ma, Z.; Han, H.; Li, Q.; Li, Z.; Chen, H. ACS Omega 2017, 2, 7048.
[140] Ciou, Y.-S.; Lin, P.-H.; Li, W.-M.; Lee, K.-M.; Liu, C.-Y. J. Org. Chem. 2017, 82, 3538.
[141] Huang, J.-H.; Lin, P.-H.; Li, W.-M.; Lee, K.-M.; Liu, C.-Y.; ChemSusChem 2017, 10, 2284.
[142] Chang, Y.-C.; Lee, K.-M.; Lai, C.-H.; Liu, C.-Y. Chem. Asian J. 2018, 13, 1510.
[143] Tian, L.; Hu, Z.; Liu, X.; Liu, Z.; Guo, P.; Xu, B.; Xue, Q.; Yip, H.-L.; Huang, F.; Cao, Y. ACS Appl. Mater. Interfaces 2019, 11, 5289.
[144] Robitaille, A.; Perea, A.; Belanger, D.; Leclerc, M. J. Mater. Chem. A 2017, 5, 18088.
[145] Wang, K.-L.; Kuo, T.-H.; Yao, C.-F.; Chang, S.-W.; Yang, Y.-S.; Huang, H.-K.; Tsai, C. J.; Horie, M. Chem. Commun. 2017, 53, 1856.
[146] Yao, C.-F.; Wang, K.-L.; Huang, H.-K.; Lin, Y.-J.; Lee, Y.-Y.; Yu, C.-W.; Tsai, C.-J.; Horie, M. Macromolecules 2017, 50, 6924.
[147] Elsawy, W.; Son, M.; Jang, J.; Kim, M. J.; Ji, Y.; Kim, T.-W.; Ko, H. C.; Elbarbary, A.; Ham, M.-H.; Lee, J.-S. ACS Macro Lett. 2015, 4, 322.
[148] Liu, B.; Bao, Y.; Ling, H.; Zhu, W.; Gong, R.; Lin, J.; Xie, L.; Yi, M.; Huang, W. Chin. J. Polym. Sci. 2016, 10, 1183.
[149] Huang, W.-Y.; Shen, Z.-Q.; Cheng, J. Z.; Liu, L.-L.; Yang, K.; Chen, X. R.; Wen, H.-R.; Liu, S.-Y. J. Mater. Chem. A 2019, 7, 24222.
[150] Lin, Y.; Zhan, X. Acc. Chem. Res. 2016, 49, 175.
[151] Kan, B.; Li, M.; Zhang, Q.; Liu, F.; Wan, X.; Wang, Y.; Ni, W.; Long, G.; Yang, X.; Feng, H.; Zuo, Y.; Zhang, M.; Huang, F.; Cao, Y.; Russell, T. P.; Chen, Y. J. Am. Chem. Soc. 2015, 137, 3886.
[152] Zhou, C.; Liang, Y.; Liu, F.; Sun, C.; Huang, X.; Xie, Z.; Huang, F.; Roncali, J.; Russell, T. P.; Cao, Y. Adv. Funct. Mater. 2014, 24, 7538.
[153] Wang, J.-L.; Liu, K.-K.; Yan, J.; Wu, Z.; Liu, F.; Xiao, F.; Chang, Z.-F.; Wu, H.-B.; Cao, Y.; Russell, T. P. J. Am. Chem. Soc. 2016, 138, 7687.
[154] Liu, S.-Y.; Liu, H.; Shen, Z.-Q.; Huang, W.-Y.; Zhong, A.-G.; Wen, H.-R. Dyes Pigm. 2019, 162, 640.
[155] Liu, S.-Y.; Cheng, J.-Z.; Zhang, X.-F.; Liu, H.; Shen, Z.-Q.; Wen, H.-R. Polym. Chem. 2019, 10, 325.
[156] Liu, H.; Zhang, X.-F.; Cheng, J.-Z.; Zhong, A.-G.; Wen, H.-R.; Liu, S.-Y. Molecules 2019, 24, 1760.
[157] Liu, S.-Y.; Wang, D.-G.; Zhong, A.-G.; Wen, H.-R. Org. Chem. Front. 2018, 5, 653.
[158] Shen, Z.-Q.; Cheng, J.-Z.; Zhang, X.-F.; Huang, W.-Y.; Wen, H.-R.; Liu, S.-Y. Prog. Chem. 2019, 31, 1221(in Chinese). (沈赵琪, 程敬招, 张小凤, 黄微雅, 温和瑞, 刘诗咏, 化学进展, 2019, 31, 1221.)
[159] Zhang, X.-F.; Cheng, J.-Z.; Liu, H.; Shan, Q.; Jia, G.; Wen, H.-R.; Liu, S.-Y. Dyes Pigm. 2020, 172, 107819.
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