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 shu

Research Progress of Benzo[1,2-b:4,5-b']difuran Organic Photovoltaic Materials

  • Corresponding author: Huo Lijun, 
  • Received Date: 21 December 2015
    Available Online: 23 January 2016

    Fund Project: 国家自然科学基金(Nos.51273203,51261160496)资助项目. (Nos.51273203,51261160496)

  • 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]

      [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]

      [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]

      [3] Li, B. Chin. J. Org. Chem. 2015, 35, 1 (in Chinese). (李保林, 有机化学, 2015, 35, 1.)

    4. [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]

      [5] Huo, L.; Ye, L.; Wu, Y.; Li, Z.; Guo, X.; Zhang, M.; Zhang, S.; Hou, J. Macromolecules2012, 45, 6923.

    6. [6]

      [6] Huang, P.; Du, J.; Biewer, M. C.; Stefan, M. C. J. Mater. Chem. A 2015, 3, 6244.

    7. [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]

      [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]

      [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]

      [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]

      [11] Bunz, U. H. F. Angew. Chem., Int. Ed. 2010, 49, 5037.

    12. [12]

      [12] Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148.

    13. [13]

      [13] Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976.

    14. [14]

      [14] Gandini, A. Green Chem., 2011,13, 1061.

    15. [15]

      [15] Takahashi, K.; Kobayashi, K. J. Org. Chem. 2000, 65, 2577.

    16. [16]

      [16] Chambers, J. J.; Kurrasch-Orbaugh, D. M.; Parker, M. A.; Nichols, D. E. J. Med. Chem. 2001, 44, 1003.

    17. [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]

      [18] Liu, B.; Chen, X.; Zou, Y.; Xiao, L.; Xu, X.; He, Y.; Li, L.; Li, Y. Macromolecules.2012, 45, 6898.

    19. [19]

      [19] Chen, X.; Liu, B.; Zou, Y.; Xiao, L.; Guo, X.; He, Y.; Li, Y. J. Mater. Chem. 2012, 22, 17724.

    20. [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]

      [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]

      [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]

      [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]

      [24] Liu, B.; Chen, X.; Zou, Y.; He, Y.; Xiao, L.; Xu, X.; Li, L.; Li, Y. Polym. Chem. 2013, 4, 470.

    25. [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]

      [26] Huo, L.; Hou, J. Polym. Chem. 2011, 2, 2453.

    27. [27]

      [27] Huo, L.; Guo, X.; Zhang, S.; Li, Y.; Huo, J. Macromolecules 2011, 44, 4035.

    28. [28]

      [28] Huo, L.; Liu, T.; Sun, X.; Cai, Y.; Heeger, A.; Sun, Y. Adv. Mater. 2015, 27, 2938.

    29. [29]

      [29] Guo, X.; Zhang, M. J.; Huo, L. J.; Hou, J. H. J. Mater. Chem. 2012, 22, 21024.

    30. [30]

      [30] Huo, L.; Hou, J.; Zhang, S.; Chen, H. Y.; Yang, Y. Angew. Chem., Int. Ed.2010, 49, 1500.

    31. [31]

      [31] Wu, Y.; Li, Z.; Guo, X.; Fan, H.; Huo, L.; Huo, J. J. Mater. Chem. 2012, 22, 21362.

    32. [32]

      [32] Zhang, Y.; Gao, L.; He, C.; Sun, Q.; Li, Y. J. Polym. Sci., Part A: Polym. Chem. 2013, 4, 1474.

    33. [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]

      [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]

      [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]

      [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]

      [37] Xiang, A.; Li, H.; Chen, S.; Liu, S. –X.; Decurtins, S.; Bai, M.; Hou, S.; Liao, J. Nanoscale 2015, 7, 7665.

    38. [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [44] Mitsui, C.; Soeda, J.; Miwa, K.; Tsuji, H.; Takeya, J.; Nakamura, E. J. Am. Chem. Soc.2012, 134, 5448.

    45. [45]

      [45] Nakano, M.; Shinamura, S.; Houchin, Y.; Osaka, I.; Miyazaki, E.; Takimiya, K. Chem. Commun.2012, 48, 5671.

    46. [46]

      [46] Nakano, M.; Mori, H.; Shinamura, S.; Takimiya, K. Chem. Mater.2012, 24, 190.

    47. [47]

      [47] Nakano, M.; Niimi, K.; Miyazaki, E.; Osaka, I.; Takimiya, K. J. Org. Chem.2012, 77, 8099.

    48. [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]

      [49] Li, S.; Yuan, J.; Deng, P.; Ma, W.; Zhang, Q. Sol. Energy Mater. Sol. Cells 2013, 118, 22.

    50. [50]

      [50] Li, S.; Yuan, Z.; Deng, P.; Sun, B.; Zhang, Q. Polym. Chem. 2014, 5, 2561

    51. [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]

      [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]

      [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]

      [54] Qiu, B.; Cui, R.; Yuan, J.; Peng, H.; Zhang, Z.; Li, Y.; Zou, Y. Phys. Chem. Chem. Phys. 2015, 17, 17592.

    55. [55]

      [55] Hu, C.; Fu, Y.; Li, S.; Xie, Z.; Zhang, Q. Polym. Chem. 2012, 3, 2949.

    56. [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]

      [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]

      [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]

      [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]

      [60] Moussallem, C.; Gohier, F.; Mallet, C.; Allain, M.; Frère, P. Tetrahedron 2012, 68, 8617.

    61. [61]

      [61] Moussalem, C.; Segut, O.; Gohier, F.; Allain, M.; Frère, P. ACS Sustainable Chem. Eng.2014, 2, 1043.

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