A pentacyclic nitrogen-bridged thienyl-phenylene-thienyl arene for donor-acceptor copolymers: Synthesis, characterization, and applications in field-effect transistors and polymer solar cells

Chemistry - An Asian Journal

Volumn 7, Issue 9, 2012, Pages 2102-2110

  Tseng, Cheng An ^a   Wu, Jhong Sian ^a   Lin, Tai Yen ^a   Kao, Wei Shun ^a   Wu, Cheng En ^a   Hsu, So Lin ^a   Liao, Yun Yu ^a   Hsu, Chain Shu ^a   Huang, Huan Yi ^a   Hsieh, You Zung ^a   Cheng, Yen Ju ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

arenes; catalysis; copolymerization; field effect transistors; solar cells

Indexed keywords

ARENES; BAND-BROADENING; BENZOTHIADIAZOLES; BUILDING BLOCKES; DONOR-ACCEPTOR COPOLYMERS; ELECTRON-DEFICIENT; FIELD-EFFECT; NITROGEN ATOM; ONE POT; OPTICAL AND ELECTRONIC PROPERTIES; OXIDATION POTENTIALS; PALLADIUM-CATALYZED AMINATION; PHENYLENE RINGS; PHOTO-INDUCED; PHOTOVOLTAIC DEVICES; POLYMER SOLAR CELLS; THIOPHENE RING;

CATALYSIS; CHARGE TRANSFER; COPOLYMERIZATION; COPOLYMERS; ELECTRONIC PROPERTIES; FIELD EFFECT TRANSISTORS; NITROGEN; SOLAR CELLS; THIOPHENE; TIN;

POLYMERS;

EID: 84865522766     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201200186     Document Type: Article

References (58)

1. A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo, Chem. Rev. 2010, 110, 3
2. G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science 1995, 270, 1789
3. S. Günes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324
4. B. C. Thompson, J. M. J. Fréchet, Angew. Chem. 2008, 120, 62
5. Angew. Chem. Int. Ed. 2008, 47, 58
6. Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 2009, 109, 5868
7. J. Chen, Y. Cao, Acc. Chem. Res. 2009, 42, 1709.
8. J. Roncali, Chem. Rev. 1997, 97, 173
9. Y. Li, Y. Zou, Adv. Mater. 2008, 20, 2952.
10. J. Roncali, Macromol. Rapid Commun. 2007, 28, 1761
11. M. Forster, K. O. Annan, U. Scherf, Macromolecules 1999, 32, 3159
12. Z. Zhu, D. Waller, R. Gaudiana, M. Morana, D. Mühlbacher, M. Scharber, C. Brabec, Macromolecules 2007, 40, 1981
13. J. Jacob, S. Sax, T. Piok, E. J. W. List, A. C. Grimsdale, K. Müllen, J. Am. Chem. Soc. 2004, 126, 6987
14. A. K. Mishra, M. Graf, F. Grasse, J. Jacob, E. J. W. List, K. Müllen, Chem. Mater. 2006, 18, 2879
15. M. B. Goldfinger, T. M. Swager, J. Am. Chem. Soc. 1994, 116, 7895
16. U. Scherf, J. Mater. Chem. 1999, 9, 1853
17. S. A. Patil, U. Scherf, A. Kadashchuk, Adv. Funct. Mater. 2003, 13, 609
18. Y. Yao, J. M. Tour, Macromolecules 1999, 32, 2455.
19. J. L. Brédas, J. P. Calbert, D. A. da Silva Filho, J. Cornil, Proc. Natl. Acad. Sci. USA 2002, 99, 5804
20. S. Ando, J.-I. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita, J. Am. Chem. Soc. 2005, 127, 5336
21. N.-S. Baek, S. K. Hau, H.-L. Yip, O. Acton, K.-S. Chen, A. K.-Y. Jen, Chem. Mater. 2008, 20, 5734
22. Y. Liang, Y. Wu, D. Feng, S.-T. Tsai, H.-J. Son, G. Li, L. Yu, J. Am. Chem. Soc. 2009, 131, 56
23. S. Shinamura, I. Osaka, E. Miyazaki, A. Nakao, M. Yamagishi, J. Takeya, K. Takimiya, J. Am. Chem. Soc. 2011, 133, 5024.
24. I. Osaka, T. Abe, S. Shinamura, E. Miyazaki, K. Takimiya, J. Am. Chem. Soc. 2010, 132, 5000
25. I. Osaka, T. Abe, S. Shinamura, K. Takimiya, J. Am. Chem. Soc. 2011, 133, 6852
26. K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki, Adv. Mater. 2011, 23, 4347
27. M. Zhang, Y. Sun, X. Guo, C. Cui, Y. He, Y. Li, Macromolecules 2011, 44, 7625.
28. H.-Y. Chen, J. Hou, S. Zhang, Y. Liang, G. Yang, Y. Yang, L. Yu, Y. Wu, G. Li, Nat. Photonics 2009, 3, 649
29. H. Zhou, L. Yang, A. C. Stuart, S. C. Price, S. Liu, W. You, Angew. Chem. 2011, 123, 3051
30. Angew. Chem. Int. Ed. 2011, 50, 2995
31. L. Huo, S. Zhang, X. Guo, F. Xu, F. Li, J. Hou, Angew. Chem. 2011, 123, 9871
32. Angew. Chem. Int. Ed. 2011, 50, 9697
33. S. C. Price, A. C. Stuart, L. Yang, H. Zhou, W. You, J. Am. Chem. Soc. 2011, 133, 4625
34. Z. He, C. Zhong, X. Huang, W.-Y. Wong, H. Wu, L. Chen, S. Su, Y. Cao, Adv. Mater. 2011, 23, 4636.
35. Y.-J. Cheng, J.-S. Wu, P.-I. Shih, C.-Y. Chang, P.-C. Jwo, W.-S. Kao, C.-S. Hsu, Chem. Mater. 2011, 23, 2361
36. C.-H. Chen, Y.-J. Cheng, M. Dubosc, C.-H. Hsieh, C.-C. Chu, C.-S. Hsu, Chem. Asian J. 2010, 5, 2483
37. C.-H. Chen, C.-H. Hsieh, M. Dubosc, Y.-J. Cheng, C.-S. Hsu, Macromolecules 2010, 43, 697
38. N. Blouin, A. Michaud, M. Leclerc, Adv. Mater. 2007, 19, 2295
39. N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletête, G. Durocher, Y. Tao, M. Leclerc, J. Am. Chem. Soc. 2008, 130, 732
40. J.-S. Wu, Y.-J. Cheng, M. Dubosc, C.-H. Hsieh, C.-Y. Chang, C.-S. Hsu, Chem. Commun. 2010, 46, 3259
41. Y.-J. Cheng, C.-H. Chen, Y.-S. Lin, C.-Y. Chang, C.-S. Hsu, Chem. Mater. 2011, 23, 5068
42. C.-H. Chen, Y.-J. Cheng, C.-Y. Chang, C.-S. Hsu, Macromolecules 2011, 44, 8415.
43. K.-T. Wong, T.-C. Chao, L.-C. Chi, Y.-Y. Chu, A. Balaiah, S.-F. Chiu, Y.-H. Liu, Y. Wang, Org. Lett. 2006, 8, 5033.
44. C.-P. Chen, S.-H. Chan, T.-C. Chao, C. Ting, B.-T. Ko, J. Am. Chem. Soc. 2008, 130, 12828
45. Y. Zhang, J. Zou, H.-L. Yip, K.-S. Chen, D. F. Zeigler, Y. Sun, A. K.-Y. Jen, Chem. Mater. 2011, 23, 2289
46. M. Zhang, X. Guo, X. Wang, H. Wang, Y. Li, Chem. Mater. 2011, 23, 4264
47. Y. Zhang, J. Zou, H.-L. Yip, K.-S. Chen, J. A. Davies, Y. Sun, A. K.-Y. Jen, Macromolecules 2011, 44, 4752
48. W. Zhang, J. Smith, S. E. Watkins, R. Gysel, M. McGehee, A. Salleo, J. Kirkpatrick, S. Ashraf, T. Anthopoulos, M. Heeney, I. McCulloch, J. Am. Chem. Soc. 2010, 132, 11437
49. Y.-C. Chen, C.-Y. Yu, Y.-L. Fan, L.-I. Hung, C.-P. Chen, C. Ting, Chem. Commun. 2010, 46, 6503.
50. J.-Y. Wang, S. K. Hau, H.-L. Yip, J. A. Davies, K.-S. Chen, Y. Zhang, Y. Sun, A. K.-Y. Jen, Chem. Mater. 2011, 23, 765
51. R. S. Ashraf, Z. Chen, D. S. Leem, H. Bronstein, W. Zhang, B. Schroeder, Y. Geerts, J. Smith, S. Watkins, T. D. Anthopoulos, H. Sirringhaus, J. C. de Mello, M. Heeney, I. McCulloch, Chem. Mater. 2011, 23, 768.
52. J. E. Donaghey, R. S. Ashraf, Y. Kim, Z. G. Huang, C. B. Nielsen, W. Zhang, B. Schroeder, C. R. G. Grenier, C. T. Brown, P. D'angelo, J. Smith, S. Watkins, K. Song, T. D. Anthopoulos, J. R. Durrant, C. K. Williams, I. McCulloch, J. Mater. Chem. 2011, 21, 18744.
53. Y. Zou, A. Najari, P. Berrouard, S. Beaupré, B. R. Aïch, Y. Tao, M. Leclerc, J. Am. Chem. Soc. 2010, 132, 5330
54. C. Piliego, T. W. Holcombe, J. D. Douglas, C. H. Woo, P. M. Beaujuge, J. M. J. Fréchet, J. Am. Chem. Soc. 2010, 132, 7595
55. T.-Y. Chu, J. Lu, S. Beaupré, Y. Zhang, J.-R. Pouliot, S. Wakim, J. Zhou, M. Leclerc, Z. Li, J. Ding, Y. Tao, J. Am. Chem. Soc. 2011, 133, 4250
56. C. M. Amb, S. Chen, K. R. Graham, J. Subbiah, C. E. Small, F. So, J. R. Reynolds, J. Am. Chem. Soc. 2011, 133, 10062.
57. H. Hart, K. Harada, C. J. F. Du, J. Org. Chem. 1985, 50, 3104.
58. W. Yue, Y. Zhao, S. Shao, H. Tian, Z. Xie, Y. Geng, F. Wang, J. Mater. Chem. 2009, 19, 2199.