Citation: Liu Ye, Yuan Jun, Zou Yingping, Li Yongfang. Research Progress of the FuranContaining Fused Ring Conjugated Organic Molecules and Polymers[J]. Acta Chimica Sinica, ;2017, 75(3): 257-270. doi: 10.6023/A16090495 shu

Research Progress of the FuranContaining Fused Ring Conjugated Organic Molecules and Polymers

Liu Ye ^a ,
Yuan Jun ^a ,
Zou Yingping ^a,*,, ,
Li Yongfang ^b

a.
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083
b.
CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Corresponding author: Zou Yingping, yingpingzou@csu.edu.cn
Received Date: 17 September 2016

Fund Project: the National Natural Science Foundation of China 51673205Project of Innovation-driven Plan in Central South University, China 2016CX035the National Natural Science Foundation of China 51173206

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Currently, as organic semiconductor materials, thiophene fused ring derivatives and the related polymers have received considerable research and application. Furan has similar chemical structure and electronic properties with thiophene due to the same main group heterocyclic atom in five-membered ring system. But furan and furan derivatives possess smaller aromaticity, higher carrier mobility, higher fluorescence quantum efficiency and better solubility, thus more and more attentions have been paid to the design and synthesis of furan-containing fused rings for the application in organic optoelectronic materials. This paper reviewed the recent research progresses of the synthetic methods, properties and applications of the conjugated organic small molecules and polymers based on the furan-containing fused rings.
- furan-containing fused rings,
- organic semiconducting material,
- five membered ring,
- conjugated organic small molecules,
- conjugated polymers
1. [1]
  Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976. doi: 10.1039/C0CC04699J
2. [2]
  Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148. doi: 10.1021/ja9093346
3. [3]
  Chen, L.; Tang, X.; Jia, K.; Tang, X. Z. Chin. J. Org. Chem. 2016, 36, 2197. doi: 10.6023/cjoc201601005
4. [4]
  Nakano, M.; Mori, H.; Shinamura, S.; Takimiya, K. Chem. Mater. 2011, 24, 190.
5. [5]
  Qian, D.; Liu, B.; Wang, S.; Himmelberger, S.; Linares, M.; Vagin, M.; Salleo, A. J. Mater. Chem. A 2015, 3, 24349. doi: 10.1039/C5TA06501A
6. [6]
  Nakano, M.; Niimi, K.; Miyazaki, E.; Osaka, I.; Takimiya, K. J. Org. Chem. 2012, 77, 8099. doi: 10.1021/jo301438t
7. [7]
  Nakano, M.; Shinamura, S.; Houchin, Y.; Osaka, I.; Miyazaki, E.; Takimiya, K. Chem. Commun. 2012, 48, 5671. doi: 10.1039/c2cc31546g
8. [8]
  Mitsui, C.; Soeda, J.; Miwa, K.; Tsuji, H.; Takeya, J.; Nakamura, E. J. Am. Chem. Soc. 2012, 134, 5448. doi: 10.1021/ja2120635
9. [9]
  Shinamura, S.; Osaka, I.; Miyazaki, E.; Nakao, A.; Yamagishi, M.; Takeya, J.; Takimiya, K. J. Am. Chem. Soc. 2011, 133, 5024. doi: 10.1021/ja110973m
10. [10]
  Nakano, M.; Shinamura, S.; Sugimoto, R.; Osaka, I.; Miyazaki, E.; Takimiya, K. Org. Lett. 2012, 14, 5448. doi: 10.1021/ol302521d
11. [11]
  Niimi, K.; Mori, H.; Miyazaki, E.; Osaka, I.; Kakizoe, H.; Takimiya, K.; Adachi, C. Chem. Commun. 2012, 48, 5892. doi: 10.1039/c2cc31960h
12. [12]
  Nakahara, K.; Mitsui, C.; Okamoto, T.; Yamagishi, M.; Miwa, K.; Sato, H.; Takeya, J. Chem. Lett. 2013, 42, 654. doi: 10.1246/cl.130133
13. [13]
  Nakahara, K.; Mitsui, C.; Okamoto, T.; Yamagishi, M.; Matsui, H.; Ueno, T.; Hirose, Y. Chem. Commun. 2014, 50, 5342. doi: 10.1039/C3CC47577H
14. [14]
  Suraru, S. L.; Burschka, C.; Würthner, F. J. Org. Chem. 2013, 79, 128.
15. [15]
  Ripaud, E.; Demeter, D.; Rousseau, T.; Boucard-Cétol, E.; Allain, M.; Po, R.; Leriche, P.; Roncali, J. Dyes Pigm. 2012, 95, 126. doi: 10.1016/j.dyepig.2012.03.021
16. [16]
  Jung, I.; Lee, J. K.; Song, K. H.; Song, K.; Kang, S. O.; Ko, J. J. Org. Chem. 2007, 72, 3652. doi: 10.1021/jo0625150
17. [17]
  Anderson, S.; Taylor, P. N.; Verschoor, G. L. Chem.-Eur. J. 2004, 10, 518. doi: 10.1002/(ISSN)1521-3765
18. [18]
  Hwu, J. R.; Chuang, K. S.; Chuang, S. H.; Tsay, S. C. Org. Lett. 2005, 7, 1545. doi: 10.1021/ol050196d
19. [19]
  Tsuji, H.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 11902. doi: 10.1021/ja074365w
20. [20]
  Tsuji, H.; Mitsui, C.; Sato, Y.; Nakamura, E. Adv. Mater. 2009, 21, 3776. doi: 10.1002/adma.v21:37
21. [21]
  Qiu, B.; Yuan, J.; Zou, Y.; He, D.; Peng, H.; Li, Y.; Zhang, Z. Org. Electron. 2016, 35, 87. doi: 10.1016/j.orgel.2016.05.010
22. [22]
  Vecchi, P. A.; Padmaperuma, A. B.; Qiao, H.; Sapochak, L. S.; Burrows, P. E. Org. Lett. 2006, 8, 4211. doi: 10.1021/ol0614121
23. [23]
  Han, C.; Xie, G.; Xu, H.; Zhang, Z.; Xie, L.; Zhao, Y.; Huang, W. Adv. Mater. 2011, 23, 2491. doi: 10.1002/adma.201100322
24. [24]
  Jeon, S. O.; Lee, J. Y. J. Mater. Chem. 2012, 22, 10537. doi: 10.1039/c2jm30473b
25. [25]
  Lee, C. W.; Yook, K. S.; Lee, J. Y. Org. Electron. 2013, 14, 1009. doi: 10.1016/j.orgel.2013.01.025
26. [26]
  Deng, L.; Li, J.; Wang, G. X.; Wu, L. Z. J. Mater. Chem. C. 2013, 1, 8140. doi: 10.1039/c3tc31893a
27. [27]
  Liu, B.; Chen, X.; He, Y.; Xiao, L.; Li, Y.; Zhou, K.; Zou, Y. RSC Adv. 2013, 3, 5366. doi: 10.1039/c3ra40268a
28. [28]
  Shi, S.; Xie, X.; Gao, C.; Shi, K.; Chen, S.; Yu, G.; Wang, H. Macromolecules 2014, 47, 616. doi: 10.1021/ma402107n
29. [29]
  Shi, S.; Shi, K.; Chen, S.; Qu, R.; Wang, L.; Wang, M.; Wang, H. J. Polym. Sci., Part A:Polym. Chem. 2014, 52, 2465. doi: 10.1002/pola.v52.17
30. [30]
  Huo, L.; Hou, J.; Zhang, S.; Chen, H. Y.; Yang, Y. Angew. Chem., Int. Ed. 2010, 49, 1500. doi: 10.1002/anie.200906934
31. [31]
  Huo, L.; Liu, T.; Sun, X.; Cai, Y.; Heeger, A. J.; Sun, Y. Adv. Mater. 2015, 27, 2938. doi: 10.1002/adma.v27.18
32. [32]
  Yuan, J.; Zou, Y.; Cui, R.; Chao, Y. H.; Wang, Z.; Ma, M.; Xiao, D. Macromolecules 2015, 48, 4347. doi: 10.1021/acs.macromol.5b00564
33. [33]
  Qiu, B.; Yuan, J.; Xiao, X.; He, D.; Qiu, L.; Zou, Y.; Li, Y. ACS Appl. Mater. Interfaces 2015, 7, 25237. doi: 10.1021/acsami.5b07066
34. [34]
  Li, S.; Yuan, Z.; Deng, P.; Sun, B.; Zhang, Q. Polym. Chem. 2014, 5, 2561. doi: 10.1039/c3py01458d
35. [35]
  Li, H.; Jiang, P.; Yi, C.; Li, C.; Liu, S. X.; Tan, S.; Decurtins, S. Macromolecules 2010, 43, 8058. doi: 10.1021/ma101693d
36. [36]
  Chen, X.; Liu, B.; Zou, Y.; Xiao, L.; Guo, X.; He, Y.; Li, Y. J. Mater. Chem. 2012, 22, 17724. doi: 10.1039/c2jm32843g
37. [37]
  Liu, B.; Chen, X.; Zou, Y.; Xiao, L.; Xu, X.; He, Y.; Li, Y. Macromolecules 2012, 45, 6898. doi: 10.1021/ma301053q
38. [38]
  Liu, B.; Chen, X.; Zou, Y.; He, Y.; Xiao, L.; Xu, X.; Li, Y. Polym. Chem. 2013, 4, 470. doi: 10.1039/C2PY20580G
39. [39]
  Huo, L.; Huang, Y.; Fan, B.; Guo, X.; Jing, Y.; Zhang, M.; Hou, J. Chem. Commun. 2012, 48, 3318. doi: 10.1039/c2cc17708k
40. [40]
  Huo, L.; Ye, L.; Wu, Y.; Li, Z.; Guo, X.; Zhang, M.; Hou, J. Macromolecules 2012, 45, 6923. doi: 10.1021/ma301254x
41. [41]
  Hong, G.; Zou, Y.; Antaris, A. L.; Diao, S.; Wu, D.; Cheng, K.; Wu, J. Z. Nat. Commun. 2014, 5.
42. [42]
  Hong, G.; Lee, J. C.; Robinson, J. T.; Raaz, U.; Xie, L.; Huang, N. F.; Dai, H. Nat. Med. 2012, 18, 1841. doi: 10.1038/nm.2995
43. [43]
  Warnan, J.; Cabanetos, C.; Labban, A. E.; Hansen, M. R.; Tassone, C.; Toney, M. F.; Beaujuge, P. M. Adv. Mater. 2014, 26, 4357. doi: 10.1002/adma.v26.25
44. [44]
  Mateker, W. R.; Heumueller, T.; Cheacharoen, R.; Sachs-Quintana, I. T.; McGehee, M. D.; Warnan, J.; Bazan, G. C. Chem. Mater. 2015, 27, 6345. doi: 10.1021/acs.chemmater.5b02341
45. [45]
  Huo, L.; Liu, T.; Fan, B.; Zhao, Z.; Sun, X.; Wei, D.; Yu, M.; Liu, Y.; Sun, Y. Adv. Mater. 2015, 27, 6969. doi: 10.1002/adma.201503023
46. [46]
  Liu, B.; Qiu, B.; Chen, X.; Xiao, L.; Li, Y.; He, Y.; Zou, Y. Polym. Chem. 2014, 5, 5002. doi: 10.1039/C4PY00392F
47. [47]
  Huang, W.; Yang, B.; Sun, J.; Liu, B.; Yang, J.; Zou, Y.; Gao, Y. Org. Electron. 2014, 15, 1050. doi: 10.1016/j.orgel.2014.02.020
48. [48]
  Bian, L.; Hai, J.; Zhu, E.; Yu, J.; Liu, Y.; Zhou, J.; Tang, W. J. Mater. Chem. A 2015, 3, 1920. doi: 10.1039/C4TA06140C
49. [49]
  Shi, Q.; Fan, H.; Liu, Y.; Hu, W.; Li, Y.; Zhan, X. Macromolecules 2011, 44, 9173. doi: 10.1021/ma2019683
50. [50]
  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. doi: 10.1002/pola.v50.20
51. [51]
  Sista, P.; Nguyen, H.; Murphy, J. W.; Hao, J.; Dei, D. K.; Palaniappan, K.; Dastoor, P. C. Macromolecules 2010, 43, 8063. doi: 10.1021/ma101709h
52. [52]
  Xiang, A.; Li, H.; Chen, S.; Liu, S. X.; Decurtins, S.; Bai, M.; Liao, J. Nanoscale 2015, 7, 7665. doi: 10.1039/C5NR00402K
53. [53]
  Li, Z.; Li, H.; Chen, S.; Froehlich, T.; Yi, C.; Schönenberger, C.; Borguet, E. J. Am. Chem. Soc. 2014, 136, 8867. doi: 10.1021/ja5034606
54. [54]
  Kobilka, B. M.; Dubrovskiy, A. V.; Ewan, M. D.; Tomlinson, A. L.; Larock, R. C.; Chaudhary, S.; Jeffries-EL, M. Chem. Commun. 2012, 48, 8919. doi: 10.1039/c2cc34070d
55. [55]
  Aeschi, Y.; Li, H.; Cao, Z.; Chen, S.; Amacher, A.; Bieri, N.; Liu, S. X. Org. Lett. 2013, 15, 5586. doi: 10.1021/ol402787d
56. [56]
  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. doi: 10.1039/c4tc00738g
57. [57]
  Cui, R.; Zou, Y.; Xiao, L.; Hsu, C. S.; Keshtov, M. L.; Godovsky, D. Y.; Li, Y. Dyes Pigm. 2015, 116, 139. doi: 10.1016/j.dyepig.2015.01.021
58. [58]
  Qiu, B.; Cui, R.; Yuan, J.; Peng, H.; Zhang, Z.; Li, Y.; Zou, Y. Phys. Chem. Chem. Phys. 2015, 17, 17592. doi: 10.1039/C5CP02127H
59. [59]
  He, D.; Qiu, L.; Zhang, Z.; Li, Y.; Pan, C.; Zou, Y. RSC Adv. 2016, 6, 62923. doi: 10.1039/C6RA09791J
60. [60]
  Zhang, H.; Guo, E.; Fang, Y.; Ren, P.; Yang, W. J. Polym. Sci., Part A:Polym. Chem. 2009, 47, 5488. doi: 10.1002/pola.v47:20
61. [61]
  Pan, X. X.; Huo, L. J. Chin. J. Org. Chem. 2016, 36, 687. doi: 10.6023/cjoc201512028
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