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

Figures(41)

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
1. [1]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
2. [2]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
3. [3]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
4. [4]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
5. [5]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
6. [6]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
7. [7]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
8. [8]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
9. [9]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
10. [10]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
11. [11]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
12. [12]
  Xiaofang DONG , Yue YANG , Shen WANG , Xiaofang HAO , Yuxia WANG , Peng CHENG . Research progress of conductive metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 14-34. doi: 10.11862/CJIC.20240388
13. [13]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
14. [14]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
15. [15]
  .
  南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积
  . CCS Chemistry, 2025, 7(0): -.
16. [16]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
17. [17]
  Mengzhen JIANG , Qian WANG , Junfeng BAI . Research progress on low-cost ligand-based metal-organic frameworks for carbon dioxide capture from industrial flue gas. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 1-13. doi: 10.11862/CJIC.20240355
18. [18]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
19. [19]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
20. [20]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(1788)
HTML views(440)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

Metrics

通讯作者: 陈斌, bchen63@163.com