Citation:
Pan Xuexue, Huo Lijun. Research Progress of Benzo[1,2-b:4,5-b']difuran Organic Photovoltaic Materials[J]. Chinese Journal of Organic Chemistry,
;2016, 36(4): 687-699.
doi:
10.6023/cjoc201512028
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In recent years, benzo[1,2-b:4,5-b']difuran (BDF) building block has got increasing attention due to its planar molecular structure, high mobilities, good solubility, rich sources, and no harm to the environment after degradation. Based on these advantages, benzodifuran unit has been widely used in organic photovoltaic materials. A highest power conversion efficiency (PCE) of 9.43% has already been achieved based on BDF unit, revealing its great potentials in organic photovoltaic materials (OPVs). In this paper, the preparation routes of BDF and the latest research progress of photovoltaic materials based on BDF unit are reviewed, and the relationships between based BDF molecular structure and its photovoltaic performances will be mainly addressed.
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[1]
[1] Liu, C.; Yi, C.; Wang, K.; Yang, Y.; Bhatta, R. S.; Tsige, M.; Xiao, S. Y.; Gong, X. ACS Appl. Mater. Inter. 2015, 7, 4928.
-
[2]
[2] Zhou, H.; Zhang, Y.; Mai, C.-K.; Collins, S. D.; Bazan, G. C.; Nguyen, T.-Q.; Heeger, A. J. Adv. Mater. 2015, 27, 1767.
-
[3]
[3] Li, B. Chin. J. Org. Chem. 2015, 35, 1 (in Chinese). (李保林, 有机化学, 2015, 35, 1.)
-
[4]
[4] Huo, L.; Huang, Y.; Fan, B.; Guo, X.; Jing, Y.; Zhang, M.; Li, Y.; Hou, J. Chem. Commun. 2012, 48, 3318.
-
[5]
[5] Huo, L.; Ye, L.; Wu, Y.; Li, Z.; Guo, X.; Zhang, M.; Zhang, S.; Hou, J. Macromolecules2012, 45, 6923.
-
[6]
[6] Huang, P.; Du, J.; Biewer, M. C.; Stefan, M. C. J. Mater. Chem. A 2015, 3, 6244.
-
[7]
[7] Bian, L.; Hai, J.; Zhu, E.; Yu, J.; Liu, Y.; Zhou, J.; Ge, G.; Tang, W. J. Mater. Chem. A 2015, 3, 1920.
-
[8]
[8] Sista, P.; Huang, P.; Gunathilake, S. S.; Bhatt, M. P.; Kularatne, R. S.; Stefan, M. C.; Biewer, M. C. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 4316.
-
[9]
[9] Huo, L.; Liu, T.; Fan, B.; Zhao, Z.; Sun, X.; Wei, D.; Yu, M.; Liu, Y.; Sun, Y. Adv. Mater. 2015, 27, 6969.
-
[10]
[10] Woo, C. H.; Beaujuge, P. M.; Holcombe, T. W.; Lee, O. P.; Frechet, J. M. J. J. Am. Chem. Soc. 2010, 132, 15547.
-
[11]
[11] Bunz, U. H. F. Angew. Chem., Int. Ed. 2010, 49, 5037.
-
[12]
[12] Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148.
-
[13]
[13] Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976.
-
[14]
[14] Gandini, A. Green Chem., 2011,13, 1061.
-
[15]
[15] Takahashi, K.; Kobayashi, K. J. Org. Chem. 2000, 65, 2577.
-
[16]
[16] Chambers, J. J.; Kurrasch-Orbaugh, D. M.; Parker, M. A.; Nichols, D. E. J. Med. Chem. 2001, 44, 1003.
-
[17]
[17] Monte, A. P.; Marona-Lewicka, D.; Parker, M. A.; Wainscott, D. B.; Nelson, D. L.; Nichols, D. E. J. Med. Chem. 1996, 39, 2953.
-
[18]
[18] Liu, B.; Chen, X.; Zou, Y.; Xiao, L.; Xu, X.; He, Y.; Li, L.; Li, Y. Macromolecules.2012, 45, 6898.
-
[19]
[19] Chen, X.; Liu, B.; Zou, Y.; Xiao, L.; Guo, X.; He, Y.; Li, Y. J. Mater. Chem. 2012, 22, 17724.
-
[20]
[20] Warnan, J.; Cabanetos, C.; Labban, A. E.; Hansen, M. R.; Tassone, C.; Toney, M. F.; Beaujuge, P. M. Adv. Mater. 2014, 26, 4357.
-
[21]
[21] Mateker, W. R.; Heumueller, T.; Cheacharoen, R.; Sachs-Quintana, I. T.; McGehee, M. D.; Warnan, J.; Beaujuge, P. M.; Liu, X.; Bazan, G. C. Chem. Mater. 2015, 27, 6345.
-
[22]
[22] Liang, Y.; Feng, D.; Wu, Y.; Tsai, S-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792.
-
[23]
[23] Wu, Y.; Li, Z.; Ma, W.; Huang, Y.; Huo, L.; Guo, X.; Zhang, M.; Ade, H.; Hou, J. Adv. Mater. 2013, 25, 3449.
-
[24]
[24] Liu, B.; Chen, X.; Zou, Y.; He, Y.; Xiao, L.; Xu, X.; Li, L.; Li, Y. Polym. Chem. 2013, 4, 470.
-
[25]
[25] Huo, L.; Li, Z.; Guo, X.; Wu, Y.; Zhang, M.; Ye, L.; Zhang, S.; Hou, J. Polym. Chem. 2013, 4, 3047.
-
[26]
[26] Huo, L.; Hou, J. Polym. Chem. 2011, 2, 2453.
-
[27]
[27] Huo, L.; Guo, X.; Zhang, S.; Li, Y.; Huo, J. Macromolecules 2011, 44, 4035.
-
[28]
[28] Huo, L.; Liu, T.; Sun, X.; Cai, Y.; Heeger, A.; Sun, Y. Adv. Mater. 2015, 27, 2938.
-
[29]
[29] Guo, X.; Zhang, M. J.; Huo, L. J.; Hou, J. H. J. Mater. Chem. 2012, 22, 21024.
-
[30]
[30] Huo, L.; Hou, J.; Zhang, S.; Chen, H. Y.; Yang, Y. Angew. Chem., Int. Ed.2010, 49, 1500.
-
[31]
[31] Wu, Y.; Li, Z.; Guo, X.; Fan, H.; Huo, L.; Huo, J. J. Mater. Chem. 2012, 22, 21362.
-
[32]
[32] Zhang, Y.; Gao, L.; He, C.; Sun, Q.; Li, Y. J. Polym. Sci., Part A: Polym. Chem. 2013, 4, 1474.
-
[33]
[33] Liu, B.; Qiu, B.; Chen, X.; Xiao, L.; Li, Y.; He, Y.; Jiang, L.; Zou, Y. Polym. Chem. 2014, 5, 5002.
-
[34]
[34] Huang, P.; Du, J.; Gunathilake, S. S.; Rainbolt, E. A.; Murphy, J. W.; Black, K. T.; Barrera, D.; Hsu, J. W.P.; Gnade, B. E.; Stefan, M. C.; Biewer, M. C. J. Mater. Chem. A 2015, 3, 6980.
-
[35]
[35] Sista, P.; Nguyen, H.; Murphy, J. W.; Hao, J.; Dei, D. K.; Palaniappan, K.; Servello, J.; Kularatne, R. S.; Gnade, B. E.; Xue, B.; Dastoor, P. C.; Biewer, M. C.; Stefan, M. C. Macromolecules 2010, 43, 8063.
-
[36]
[36] Keller, S.; Yi, C.; Li, C.; Liu, S.-X.; Blum, C.; Frei, G.; Sereda, O.; Neels, A.; Wandlowski, T.; Decurtins, S. Org. Biomol. Chem. 2011, 9, 6410.
-
[37]
[37] Xiang, A.; Li, H.; Chen, S.; Liu, S. –X.; Decurtins, S.; Bai, M.; Hou, S.; Liao, J. Nanoscale 2015, 7, 7665.
-
[38]
[38] Li, Z.; Li, H.; Chen, S.; Froehlich, T.; Yi, C.; Schonenberger, C.; Calame, M.; Decurtins, S.; Liu, S. X.; Borguet, E. J. Am. Chem. Soc.2014, 136, 8867.
-
[39]
[39] Li, H.; Tang, P.; Zhao, Y.; Liu, S.-X.; Aeschi, Y.; Deng, L.; Braun, J.; Zhao, B.; Liu, Y.; Tan, S.; Meier, W.; Decurtins, S. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 2935.
-
[40]
[40] Yi, C.; Blum, C.; Lehmann, M.; Keller, S.; Liu, S. X.; Frei, G.; Neels, A.; Hauser, J.; Schurch, S.; Decurtins, S. J. Org. Chem.2010, 75, 3350.
-
[41]
[41] Li, H.; Jiang, P.; Yi, C.; Li, C.; Liu, S.-X.; Tan, S.; Zhao, B.; Braun, J. R.; Meier, W.; Wandlowski, T.; Decurtins, S. Macromolecules 2010, 43, 8058.
-
[42]
[42] Kobilka, B. M.; Dubrovskiy, A. V.; Ewan, M. D.; Tomlinson, A. L.; Larock, R. C.; Chaudhary, S.; Jeffries, E. M. Chem. Commun.2012, 48, 8919.
-
[43]
[43] Kobilka, B. M.; Hale, B. J.; Ewan, M. D.; Dubrovskiy, A. V.; Nelson, T. L.; Duzhko, V.; Jeffries-El, M. J. Polym. Sci., Part A: Polym. Chem. 2013, 4, 5329.
-
[44]
[44] Mitsui, C.; Soeda, J.; Miwa, K.; Tsuji, H.; Takeya, J.; Nakamura, E. J. Am. Chem. Soc.2012, 134, 5448.
-
[45]
[45] Nakano, M.; Shinamura, S.; Houchin, Y.; Osaka, I.; Miyazaki, E.; Takimiya, K. Chem. Commun.2012, 48, 5671.
-
[46]
[46] Nakano, M.; Mori, H.; Shinamura, S.; Takimiya, K. Chem. Mater.2012, 24, 190.
-
[47]
[47] Nakano, M.; Niimi, K.; Miyazaki, E.; Osaka, I.; Takimiya, K. J. Org. Chem.2012, 77, 8099.
-
[48]
[48] Liu, B.; Chen, X.; He, Y.; Xiao, L.; Li, Y.; Zhou, K.; Fan, L.; Zou, Y. RSC Adv. 2013, 3, 5366.
-
[49]
[49] Li, S.; Yuan, J.; Deng, P.; Ma, W.; Zhang, Q. Sol. Energy Mater. Sol. Cells 2013, 118, 22.
-
[50]
[50] Li, S.; Yuan, Z.; Deng, P.; Sun, B.; Zhang, Q. Polym. Chem. 2014, 5, 2561
-
[51]
[51] Aeschi, Y.; Li, H.; Cao, Z.; Chen, S.; Amacher, A.; Bieri, N.; Ozen, B.; Hauser, J.; Decurtins, S.; Tan, S.; Liu, S.-X. Org. Lett. 2013, 15, 5586.
-
[52]
[52] Fan, L.; Cui, R.; Guo, X.; Qian, D.; Qiu, B.; Yuan, J.; Li, Y.; Huang, W.; Yang, J.; Liu, W.; Xu, X.; Li, L.; Zou, Y. J. Mater. Chem. C 2014, 2, 5651.
-
[53]
[53] Liu, B.; Chen, X.; He, Y.; Li, Y.; Xu, X.; Xiao, L.; Li, L.; Zou, Y. J. Mater. Chem. A 2013, 1, 570.
-
[54]
[54] Qiu, B.; Cui, R.; Yuan, J.; Peng, H.; Zhang, Z.; Li, Y.; Zou, Y. Phys. Chem. Chem. Phys. 2015, 17, 17592.
-
[55]
[55] Hu, C.; Fu, Y.; Li, S.; Xie, Z.; Zhang, Q. Polym. Chem. 2012, 3, 2949.
-
[56]
[56] 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.
-
[57]
[57] Kan, B.; Zhang, Q.; Li, M.; Wan, X.; Ni, W.; Long, G.; Wang, Y.; Yang, X.; Feng, H.; Chen, Y. J. Am. Chem. Soc.2014, 136, 15529.
-
[58]
[58] Santos-Perez, J.; Crespo-Hernandez, C. E.; Reichardt, C.; Cabrera, C. R.; Feliciano-Ramos, I.; Arroyo-Ramirez, L.; Meador, M. A. J. Phys. Chem. A 2011, 115, 4157.
-
[59]
[59] Watanabe, M.; Su, W. T.; Chang, Y. J.; Chao, T. H.; Wen, Y. S.; Chow, T. J. Chem. Asian J.2013, 8, 60.
-
[60]
[60] Moussallem, C.; Gohier, F.; Mallet, C.; Allain, M.; Frère, P. Tetrahedron 2012, 68, 8617.
-
[61]
[61] Moussalem, C.; Segut, O.; Gohier, F.; Allain, M.; Frère, P. ACS Sustainable Chem. Eng.2014, 2, 1043.
-
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