"conformation Locked" Strong Electron-Deficient Poly(p -Phenylene Vinylene) Derivatives for Ambient-Stable n-Type Field-Effect Transistors: Synthesis, Properties, and Effects of Fluorine Substitution Position

Journal of the American Chemical Society

Volumn 136, Issue 5, 2014, Pages 2135-2141

  Lei, Ting ^a   Xia, Xin ^b   Wang, Jie Yu ^a   Liu, Chen Jiang ^b   Pei, Jian ^a  

^a PEKING UNIVERSITY   (China)

^b XINJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT CONDITIONS; FLUORINE SUBSTITUTION; HIGH ELECTRON MOBILITY; INTERCHAIN INTERACTIONS; LOCKED CONFORMATIONS; POLY(P-PHENYLENE VINYLENE) DERIVATIVES; POLYMER FIELD EFFECT TRANSISTORS; STACKING DISTANCES;

CONFORMATIONS; FIELD EFFECT TRANSISTORS; FLUORINATION; FLUORINE; HALOGENATION; LOCKS (FASTENERS);

POLYMERS;

FLUORINE; POLYMER; VINYL DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; ATOM; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DECOMPOSITION; ELECTROCHEMISTRY; ELECTRON; ELECTRON TRANSPORT; ENCAPSULATION; FLUORINATION; HYDROGEN BOND; MOLECULAR WEIGHT; POLYMERIZATION; SEMICONDUCTOR; SOLID STATE; STILLE REACTION; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE; THERMOSTABILITY;

EID: 84893715686     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja412533d     Document Type: Article

References (50)

1. Heeger, A. J. Chem. Soc. Rev. 2010, 39, 2354-2371
2. Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. J. Am. Chem. Soc. 2013, 135, 6724-6746
3. Nielsen, C. B.; Turbiez, M.; McCulloch, I. Adv. Mater. 2013, 25, 1859-1880
4. Yuen, J. D.; Wudl, F. Energy Environ. Sci. 2013, 6, 392-406
5. Tsao, H. N.; Cho, D. M.; Park, I.; Hansen, M. R.; Mavrinskiy, A.; Yoon, D. Y.; Graf, R.; Pisula, W.; Spiess, H. W.; Müllen, K. J. Am. Chem. Soc. 2011, 133, 2605-2612
6. Tseng, H.-R.; Ying, L.; Hsu, B. B. Y.; Perez, L. A.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Nano Lett. 2012, 12, 6353-6357
7. Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268-284
8. Yan, H.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dotz, F.; Kastler, M.; Facchetti, A. Nature 2009, 457, 679-686
9. Fan, J.; Yuen, J. D.; Cui, W.; Seifter, J.; Mohebbi, A. R.; Wang, M.; Zhou, H.; Heeger, A.; Wudl, F. Adv. Mater. 2012, 24, 6164-6168
10. Yuen, J. D.; Fan, J.; Seifter, J.; Lim, B.; Hufschmid, R.; Heeger, A. J.; Wudl, F. J. Am. Chem. Soc. 2011, 133, 20799-20807
11. Lee, J.; Han, A. R.; Yu, H.; Shin, T. J.; Yang, C.; Oh, J. H. J. Am. Chem. Soc. 2013, 135, 9540-9547
12. Kang, I.; Yun, H.-J.; Chung, D. S.; Kwon, S.-K.; Kim, Y.-H. J. Am. Chem. Soc. 2013, 135, 14896-14899
13. Li, J.; Zhao, Y.; Tan, H. S.; Guo, Y.; Di, C.-A.; Yu, G.; Liu, Y.; Lin, M.; Lim, S. H.; Zhou, Y.; Su, H.; Ong, B. S. Sci. Rep. 2012, 2, 754
14. Stalder, R.; Mei, J.; Graham, K. R.; Estrada, L. A.; Reynolds, J. R. Chem. Mater. 2014, 26, 664-678
15. Mei, J.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. J. Am. Chem. Soc. 2011, 133, 20130-20133
16. Lei, T.; Cao, Y.; Zhou, X.; Peng, Y.; Bian, J.; Pei, J. Chem. Mater. 2012, 24, 1762-1770
17. Lei, T.; Cao, Y.; Fan, Y.; Liu, C.-J.; Yuan, S.-C.; Pei, J. J. Am. Chem. Soc. 2011, 133, 6099-6101
18. Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208-2267
19. Li, H.; Kim, F. S.; Ren, G.; Jenekhe, S. A. J. Am. Chem. Soc. 2013, 135, 14920-14923
20. Takeda, Y.; Andrew, T. L.; Lobez, J. M.; Mork, A. J.; Swager, T. M. Angew. Chem., Int. Ed. 2012, 51, 9042-9046
21. Lee, J.-K.; Gwinner, M. C.; Berger, R.; Newby, C.; Zentel, R.; Friend, R. H.; Sirringhaus, H.; Ober, C. K. J. Am. Chem. Soc. 2011, 133, 9949-9951
22. Babel, A.; Jenekhe, S. A. J. Am. Chem. Soc. 2003, 125, 13656-13657
23. Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296-1323
24. Tang, M. L.; Bao, Z. Chem. Mater. 2011, 23, 446-455
25. Lei, T.; Dou, J.-H.; Ma, Z.-J.; Liu, C.-J.; Wang, J.-Y.; Pei, J. Chem. Sci. 2013, 4, 2447-2452
26. Chen, H.-Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nat. Photon. 2009, 3, 649-653
27. Bronstein, H.; Frost, J. M.; Hadipour, A.; Kim, Y.; Nielsen, C. B.; Ashraf, R. S.; Rand, B. P.; Watkins, S.; McCulloch, I. Chem. Mater. 2013, 25, 277-285
28. Park, J. H.; Jung, E. H.; Jung, J. W.; Jo, W. H. Adv. Mater. 2013, 25, 2583-2588
29. Lei, T.; Dou, J.-H.; Ma, Z.-J.; Yao, C.-H.; Liu, C.-J.; Wang, J.-Y.; Pei, J. J. Am. Chem. Soc. 2012, 134, 20025-20028
30. Prins, P.; Grozema, F. C.; Schins, J. M.; Patil, S.; Scherf, U.; Siebbeles, L. D. A. Phys. Rev. Lett. 2006, 96, 146601
31. Noriega, R.; Rivnay, J.; Vandewal, K.; Koch, F. P. V.; Stingelin, N.; Smith, P.; Toney, M. F.; Salleo, A. Nat. Mater. 2013, 12, 1038-1044
32. Lei, T.; Dou, J.-H.; Cao, X.-Y.; Wang, J.-Y.; Pei, J. J. Am. Chem. Soc. 2013, 135, 12168-12171
33. Yan, Z.; Sun, B.; Li, Y. Chem. Commun. 2013, 49, 3790-3792
34. Lei, T.; Dou, J. H.; Cao, X. Y.; Wang, J. Y.; Pei, J. Adv. Mater. 2013, 25, 6589-6593
35. Di Pietro, R.; Fazzi, D.; Kehoe, T. B.; Sirringhaus, H. J. Am. Chem. Soc. 2012, 134, 14877-14889
36. Lei, T.; Dou, J.-H.; Pei, J. Adv. Mater. 2012, 24, 6457-6461
37. Zhang, F.; Hu, Y.; Schuettfort, T.; Di, C.-A.; Gao, X.; McNeill, C. R.; Thomsen, L.; Mannsfeld, S. C. B.; Yuan, W.; Sirringhaus, H.; Zhu, D. J. Am. Chem. Soc. 2013, 135, 2338-2349
38. Wen, Y.; Liu, Y.; Guo, Y.; Yu, G.; Hu, W. Chem. Rev. 2011, 111, 3358-3406
39. Kim, J.; Swager, T. M. Nature 2001, 411, 1030-1034
40. Steyrleuthner, R.; Schubert, M.; Howard, I.; Klaumünzer, B.; Schilling, K.; Chen, Z.; Saalfrank, P.; Laquai, F.; Facchetti, A.; Neher, D. J. Am. Chem. Soc. 2012, 134, 18303-18317
41. Zhou, N.; Guo, X.; Ortiz, R. P.; Li, S.; Zhang, S.; Chang, R. P. H.; Facchetti, A.; Marks, T. J. Adv. Mater. 2012, 24, 2242-2248
42. Usta, H.; Newman, C.; Chen, Z.; Facchetti, A. Adv. Mater. 2012, 24, 3678-3684
43. Chen, Z.; Zheng, Y.; Yan, H.; Facchetti, A. J. Am. Chem. Soc. 2009, 131, 8-9
44. Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 7787-7799
45. Niedzialek, D.; Lemaur, V.; Dudenko, D.; Shu, J.; Hansen, M. R.; Andreasen, J. W.; Pisula, W.; Müllen, K.; Cornil, J.; Beljonne, D. Adv. Mater. 2013, 25, 1939-1947
46. Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Brédas, J.-L. Chem. Rev. 2007, 107, 926-952
47. Osaka, I.; Abe, T.; Shinamura, S.; Takimiya, K. J. Am. Chem. Soc. 2011, 133, 6852-6860
48. Rieger, R.; Beckmann, D.; Mavrinskiy, A.; Kastler, M.; Müllen, K. Chem. Mater. 2010, 22, 5314-5318
49. Lei, T.; Wang, J.-Y.; Pei, J. Chem. Mater. 2014, 26, 594-603
50. Mei, J.; Bao, Z. Chem. Mater. 2014, 26, 604-615