基于苯并[1,2-b:4,5-b']二呋喃共轭单元有机光伏材料的研究进展

doi:10.6023/cjoc201512028

摘要/Abstract

近几年,苯并[1,2-b:4,5-b']二呋喃(benzo[1,2-b:4,5-b']difuran,BDF)由于其平面性好、电荷迁移率高、溶解性好、生产来源丰富、可生物降解等优点,得到了越来越多的关注,并被广泛应用于有机光伏分子的设计中.目前所报道的基于该共轭单元的有机光伏器件(OPV)的光电转化效率(PCE)最高已达到了9.43%,展示了巨大的应用前景.系统地介绍了BDF共轭单元的制备路线及基于BDF单元的光伏材料的最新研究进展,重点讨论了基于BDF单元给体材料结构的变化对光伏性能的影响.

关键词: 苯并[1,2-b:4,5-b']二呋喃, 研究进展, 共轭聚合物, 聚合物太阳能电池

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.

Key words: benzo[1,2-b:4,5-b']difuran, research progress, conjugated polymer, polymer solar cell

引用此文

潘雪雪, 霍利军. 基于苯并[1,2-b:4,5-b']二呋喃共轭单元有机光伏材料的研究进展[J]. 有机化学, 2016, 36(4): 687-699.

Pan Xuexue, Huo Lijun. Research Progress of Benzo[1,2-b:4,5-b']difuran Organic Photovoltaic Materials[J]. Chin. J. Org. Chem., 2016, 36(4): 687-699.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[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] 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] Li, B. Chin. J. Org. Chem. 2015, 35, 1 (in Chinese). (李保林, 有机化学, 2015, 35, 1.)
[4] Huo, L.; Huang, Y.; Fan, B.; Guo, X.; Jing, Y.; Zhang, M.; Li, Y.; Hou, J. Chem. Commun. 2012, 48, 3318.
[5] Huo, L.; Ye, L.; Wu, Y.; Li, Z.; Guo, X.; Zhang, M.; Zhang, S.; Hou, J. Macromolecules2012, 45, 6923.
[6] Huang, P.; Du, J.; Biewer, M. C.; Stefan, M. C. J. Mater. Chem. A 2015, 3, 6244.
[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] 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] Huo, L.; Liu, T.; Fan, B.; Zhao, Z.; Sun, X.; Wei, D.; Yu, M.; Liu, Y.; Sun, Y. Adv. Mater. 2015, 27, 6969.
[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] Bunz, U. H. F. Angew. Chem., Int. Ed. 2010, 49, 5037.
[12] Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148.
[13] Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976.
[14] Gandini, A. Green Chem., 2011,13, 1061.
[15] Takahashi, K.; Kobayashi, K. J. Org. Chem. 2000, 65, 2577.
[16] Chambers, J. J.; Kurrasch-Orbaugh, D. M.; Parker, M. A.; Nichols, D. E. J. Med. Chem. 2001, 44, 1003.
[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] Liu, B.; Chen, X.; Zou, Y.; Xiao, L.; Xu, X.; He, Y.; Li, L.; Li, Y. Macromolecules.2012, 45, 6898.
[19] Chen, X.; Liu, B.; Zou, Y.; Xiao, L.; Guo, X.; He, Y.; Li, Y. J. Mater. Chem. 2012, 22, 17724.
[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] 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] Liang, Y.; Feng, D.; Wu, Y.; Tsai, S-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792.
[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] Liu, B.; Chen, X.; Zou, Y.; He, Y.; Xiao, L.; Xu, X.; Li, L.; Li, Y. Polym. Chem. 2013, 4, 470.
[25] Huo, L.; Li, Z.; Guo, X.; Wu, Y.; Zhang, M.; Ye, L.; Zhang, S.; Hou, J. Polym. Chem. 2013, 4, 3047.
[26] Huo, L.; Hou, J. Polym. Chem. 2011, 2, 2453.
[27] Huo, L.; Guo, X.; Zhang, S.; Li, Y.; Huo, J. Macromolecules 2011, 44, 4035.
[28] Huo, L.; Liu, T.; Sun, X.; Cai, Y.; Heeger, A.; Sun, Y. Adv. Mater. 2015, 27, 2938.
[29] Guo, X.; Zhang, M. J.; Huo, L. J.; Hou, J. H. J. Mater. Chem. 2012, 22, 21024.
[30] Huo, L.; Hou, J.; Zhang, S.; Chen, H. Y.; Yang, Y. Angew. Chem., Int. Ed.2010, 49, 1500.
[31] Wu, Y.; Li, Z.; Guo, X.; Fan, H.; Huo, L.; Huo, J. J. Mater. Chem. 2012, 22, 21362.
[32] Zhang, Y.; Gao, L.; He, C.; Sun, Q.; Li, Y. J. Polym. Sci., Part A: Polym. Chem. 2013, 4, 1474.
[33] Liu, B.; Qiu, B.; Chen, X.; Xiao, L.; Li, Y.; He, Y.; Jiang, L.; Zou, Y. Polym. Chem. 2014, 5, 5002.
[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] 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] 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] Xiang, A.; Li, H.; Chen, S.; Liu, S. –X.; Decurtins, S.; Bai, M.; Hou, S.; Liao, J. Nanoscale 2015, 7, 7665.
[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] 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] 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] 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] 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] 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] Mitsui, C.; Soeda, J.; Miwa, K.; Tsuji, H.; Takeya, J.; Nakamura, E. J. Am. Chem. Soc.2012, 134, 5448.
[45] Nakano, M.; Shinamura, S.; Houchin, Y.; Osaka, I.; Miyazaki, E.; Takimiya, K. Chem. Commun.2012, 48, 5671.
[46] Nakano, M.; Mori, H.; Shinamura, S.; Takimiya, K. Chem. Mater.2012, 24, 190.
[47] Nakano, M.; Niimi, K.; Miyazaki, E.; Osaka, I.; Takimiya, K. J. Org. Chem.2012, 77, 8099.
[48] Liu, B.; Chen, X.; He, Y.; Xiao, L.; Li, Y.; Zhou, K.; Fan, L.; Zou, Y. RSC Adv. 2013, 3, 5366.
[49] Li, S.; Yuan, J.; Deng, P.; Ma, W.; Zhang, Q. Sol. Energy Mater. Sol. Cells 2013, 118, 22.
[50] Li, S.; Yuan, Z.; Deng, P.; Sun, B.; Zhang, Q. Polym. Chem. 2014, 5, 2561
[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] 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] Liu, B.; Chen, X.; He, Y.; Li, Y.; Xu, X.; Xiao, L.; Li, L.; Zou, Y. J. Mater. Chem. A 2013, 1, 570.
[54] Qiu, B.; Cui, R.; Yuan, J.; Peng, H.; Zhang, Z.; Li, Y.; Zou, Y. Phys. Chem. Chem. Phys. 2015, 17, 17592.
[55] Hu, C.; Fu, Y.; Li, S.; Xie, Z.; Zhang, Q. Polym. Chem. 2012, 3, 2949.
[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] 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] 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] Watanabe, M.; Su, W. T.; Chang, Y. J.; Chao, T. H.; Wen, Y. S.; Chow, T. J. Chem. Asian J.2013, 8, 60.
[60] Moussallem, C.; Gohier, F.; Mallet, C.; Allain, M.; Frère, P. Tetrahedron 2012, 68, 8617.
[61] Moussalem, C.; Segut, O.; Gohier, F.; Allain, M.; Frère, P. ACS Sustainable Chem. Eng.2014, 2, 1043.