Studies on the generation of metalating species equivalent to the Knochel-Hauser base in the dehydrobrominative polymerization of thiophene derivatives

Organometallics

Volumn 31, Issue 6, 2012, Pages 2263-2267

  Tamba, Shunsuke ^a   Mitsuda, Shinobu ^a   Tanaka, Fujimaru ^a   Sugie, Atsushi ^a   Mori, Atsunori ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; NICKEL CATALYST; POLY (3-HEXYLTHIOPHENE); POLY-THIOPHENE; REGIO-REGULAR; THIOPHENE DERIVATIVES;

AMIDES; CATALYSTS; MAGNESIUM; MOLECULAR WEIGHT DISTRIBUTION; POLYCONDENSATION; THIOPHENE;

CARRIER MOBILITY;

EID: 84859119898     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om201209z     Document Type: Article

References (69)

1. Sirringhaus, H.; Tessler, N.; Friend, R. H. Science 1998, 280, 1741
2. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, W. W.; Herwig, P.; deLeeuw, D. M. Nature 1999, 401, 685
3. Kim, Y.; Cook, S.; Tuladhar, S. M.; Choulis, S. A.; Nelson, J.; Durrant, J. R.; Bradley, D. D. C.; Giles, M.; McCulloch, I.; Ha, C.-S.; Ree, M. Nat. Mater. 2006, 5, 197
4. Woo, C. H.; Thompson, B. C.; Kim, B. J.; Toney, M. F.; Fréchet, J. M. J. J. Am. Chem. Soc. 2008, 130, 16324
5. Roncali, J. Chem. Rev. 1997, 97, 173
6. Günes, S.; Neugebauer, H.; Sarisiftci, N. S. Chem. Rev. 2007, 107, 1324
7. Cheng, Y.-J.; Yang, S.-H.; Hsu, C.-S. Chem. Rev. 2009, 109, 5868
8. Chen, F.; Mehta, P. G.; Takiff, L.; McCullough, R. D. J. Mater. Chem. 1996, 6, 1763
9. Gangopadhyay, P.; Koeckelberghs, G.; Persoons, A. Chem. Mater. 2011, 23, 516
10. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537
11. Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897
12. Chen, T. A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087
13. Chen, T.-A.; O'Brien, R. D.; Rieke, R. D. Macromolecules 1993, 26, 3462
14. Chen, T. A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233
15. Wu, X.; Chen, T.-A.; Rieke, R. D. Macromolecules 1996, 29, 7671
16. Loewe, R. S.; Khersonsky, S. M.; McCullough, R. D. Adv. Mater. 1999, 11, 250
17. Sheina, E. E.; Liu, J.; Iovu, M. C.; Laird, D. W.; McCullough, R. D. Macromolecules 2004, 37, 3526
18. Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649
19. Jeffries-El, M.; Sauvé, G.; McCullough, R. D. Macromolecules 2005, 38, 10346
20. Stefan, M. C.; Javier, A. E.; Osaka, I.; McCullough, R. D. Macromolecules 2009, 42, 30
21. Yokoyama, A.; Miyakoshi, R.; Yokozawa, T. Macromolecules 2004, 37, 1169
22. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. J. Am. Chem. Soc. 2005, 127, 17542
23. Yokozawa, T.; Yokoyama, A. Chem. Rev. 2009, 109, 5595
24. McCullough, R. D. Adv. Mater. 1998, 10, 93
25. Osaka, I.; McCullough, R. D. Acc. Chem. Res. 2008, 41, 1202
26. McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 1, 70
27. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904
28. Wang, Q.; Takita, R.; Kikuzaki, T.; Ozawa, F. J. Am. Chem. Soc. 2010, 132, 11420
29. Hassan, J.; Shultz, E.; Gozzi, C.; Lemaire, M. J. Mol. Catal. A: Chem. 2003, 195, 125
30. Tamba, S.; Tanaka, S.; Okubo, Y.; Okamoto, S.; Meguro, H.; Mori, A. Chem. Lett. 2011, 40, 398
31. Tamba, S.; Shono, K.; Sugie, A.; Mori, A. J. Am. Chem. Soc. 2011, 133, 9700
32. Tanaka, S.; Tamba, S.; Tanaka, D.; Sugie, A.; Mori, A. J. Am. Chem. Soc. 2011, 133, 16734
33. Mori, A. J. Synth. Org. Chem. Jpn. 2011, 69, 1202
34. Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958
35. Lin, W.; Baron, O.; Knochel, P. Org. Lett. 2006, 8, 5673
36. Clososki, G. C.; Rohbogner, C. J.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7681
37. Rohbogner, C. J.; Clososki, G. C.; Knochel, P. Angew. Chem., Int. Ed. 2008, 47, 1503
38. Stoll, A. H.; Knochel, P. Org. Lett. 2008, 10, 113
39. Mosrin, M.; Knochel, P. Org. Lett. 2008, 10, 2497
40. Piller, F. M.; Knochel, P. Org. Lett. 2009, 11, 445
41. Hauser, C. R.; Walker, H. G. J. Am. Chem. Soc. 1947, 69, 295
42. Frostick, F. C.; Hauser, C. R. J. Am. Chem. Soc. 1949, 71, 1350
43. Eaton, P. E.; Lee, C.-H.; Xiong, Y. J. Am. Chem. Soc. 1989, 111, 8016
44. Haag, B.; Mosrin, M.; Ila, H.; Malakhov, V.; Knochel, P. Angew. Chem., Int. Ed. 2011, 50, 9794
45. Mulvey, R. E. Organometallics 2006, 25, 1060
46. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802
47. Garcalvarez, P.; Graham, D. V.; Hevia, E.; Kennedy, A. R.; Klett, J.; Mulvey, R. E.; O'Hara, C. T.; Weatherstone, S. Angew. Chem., Int. Ed. 2008, 47, 8079
48. Eaton, P. E.; Xiong, Y.; Gilardi, R. J. Am. Chem. Soc. 1993, 115, 10195
49. Clososki, G. C.; Rohbogner, C. J.; Knochel, P. Angew. Chem. 2007, 119, 7825
50. Angew. Chem., Int. Ed. 2007, 46, 7681.
51. Awad, H.; Mongin, F.; Trécourt, F.; Quéguiner, G.; Marsais, F.; Blanco, F.; Abarca, B.; Ballesteros, R. Tetrahedron Lett. 2004, 45, 6697
52. Awad, H.; Mongin, F.; Trécourt, F.; Quéguiner, G.; Marsais, F. Tetrahedron Lett. 2004, 45, 7873
53. Bayh, O.; Awad, H.; Mongin, F.; Hoarau, C.; Trécourt, F.; Quéguiner, G.; Marsais, F.; Blanco, F.; Abarca, B.; Ballesteros, R. Tetrahedron 2005, 61, 4779
54. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748-8750
55. Kondo, Y.; Morey, J. M.; Morgan, J. C.; Naka, H.; Nobuto, D.; Raithby, P. R.; Uchiyama, M.; Wheatley, A. E. H. J. Am. Chem. Soc. 2007, 129, 12734
56. L'Helgoual'ch, J.-M.; Seggio, A.; Chevallier, F.; Yonehara, M.; Jeanneau, E.; Uchiyama, M.; Mongin, F. J. Org. Chem. 2008, 73, 177
57. Clegg, W.; Conway, B.; Hevia, E.; McCall, M. D.; Russo, L.; Mulvey, R. E. J. Am. Chem. Soc. 2009, 131, 2375
58. Lohwasser, R. H.; Thelakkat, M. Macromolecules 2011, 44, 3388
59. Wu, S.; Huang, L.; Tian, H.; Geng, Y.; Wang, F. Macromolecules 2011, 44, 7558
60. Lamps, J.-P.; Catala, J.-M. Macromolecules 2011, 44, 7962
61. Lanni, E. L.; McNeil, A. J. Macromolecules 2010, 43, 8039
62. Bronstein, H. A.; Luscombe, C. K. J. Am. Chem. Soc. 2009, 131, 12894
63. Smeets, A.; Willot, P.; Winter, J. D.; Gerbaux, P.; Verbiest, T.; Koeckelberghs, G. Macromolecules 2011, 44, 6017
64. Senkovskyy, V.; Sommer, M.; Tkachov, R.; Komber, H.; Huck, W. T. S.; Kiriy, A. Macromolecules 2010, 43, 10157
65. Doubina, N.; Paniagua, S. A.; Soldatova, A. V.; Jen, A. K. Y.; Marder, S. R.; Luscombe, C. K. Macromolecules 2011, 44, 512
66. Smeets, A.; Van den Bergh, K.; Winter, J. D.; Gerbaux, P.; Verbiest, T.; Koeckelberghs, G. Macromolecules 2009, 42, 7638
67. Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2009, 131, 17052
68. Booth, G.; Chatt, J. J. Chem. Soc. 1965, 3239
69. Black, T. H.; McDermott, T. S.; Brown, G. A. Tetrahedron Lett. 1991, 32, 6501