Steric stabilization effects in nickel-catalyzed regioregular Poly(3-hexylthiophene) synthesis

Macromolecules

Volumn 42, Issue 24, 2009, Pages 9387-9389

  Boyd, Shane D ^a   Jen, Alex K Y ^a   Luscombe, Christine K ^a  

^a University of Washington   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIBROMOTHIOPHENE; DIETHYL ETHERS; ETHYLENE DIAMINE; IODOBENZENE; N-BUTYLLITHIUM; POLY-3-HEXYLTHIOPHENE; REGIO-REGULAR; REGIOREGULAR P3HT; STERIC STABILIZATION; TETRAMETHYL; THIOPHENE MONOMERS;

CARRIER MOBILITY; DICHLOROMETHANE; DISTILLATION; ETHERS; IODINE; MONOMERS; NICKEL ALLOYS; ORGANIC POLYMERS; STABILIZATION; THIOPHENE;

SYNTHESIS (CHEMICAL);

EID: 74049158293     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma902190p     Document Type: Article

References (38)

1. lovu, M. C.; Jeffries-El, M.; Sheina, E. E.; Cooper, J. R.; McCullough, R. D. Polymer 2005, 46, 8582.
2. McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70.
3. McCullough, R. D. Adv. Mater. 1998,10, 93.
4. 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, E. W.; Herwig, P.; De Leeuw, D. M. Nature 1999, 401, 685.
5. Ma, W.; Yang, C.; Gong, X.; Lee, K.; Heeger, A. J. Adv. Funct. Mater. 2005,15, 1617.
6. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007,107, 1324.
7. Loewe, R. S.; Khersonsky, S. M.; McCullough, R. D. Adv. Mater. 1999,11, 250.
8. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. J. Am. Chem. Soc. 2005,127, 17542.
9. Reyes-Reyes, M.; Kim, K.; Carroll, D. L. Appl. Phys. Lett. 2005, 87.
10. Sacco, A.; Mastrorilli, P. J. Chem. Soc., Dalton Trans. 1994, 2761.
11. Senkovskyy, V.; Khanduyeva, N.; Komber, H.; Oertel, U.; Stamm, M.; Kuckling, D.; Kiriy, A. J. Am. Chem. Soc. 2007,129, 6626.
12. Sheina, E. E.; Liu, J. S.; Iovu, M. C; Laird, D. W.; McCullough, R. D. Maeromoleeules 2004, 37, 3526.
13. Sontag, S. K.; Marshall, N.; Locklin, J. Chem. Comm. 2009, 3354.
14. Yokoyama, A.; Suzuki, H.; Kubota, Y.; Ohuchi, K.; Higashimura, H.; Yokozawa, T. J. Am. Chem. Soc. 2007,129, 7236.
15. Zeller, A.; Herdtweck, E.; Strassner, T. Eur. J. Inorg. Chem. 2003, 1802.
16. Bao, Z. N.; Lovinger, A. J. Chem. Mater. 1999,11, 2607.
17. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993,58, 904.
18. Chen, T. A.; Wu, X. M.; Rieke, R. D. J. Am. Chem. Soc. 1995,117, 233.
19. Wu, X.; Chen, T.; Rieke, R. D. Macromolecules 1996, 29,1611.
20. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. J. Polym. Sci., Part A 2008, 46, 753.
21. Yokoyama, A.; Miyakoshi, R.; Yokozawa, T. Macromolecules 2004,57,1169.
22. Bronstein, H.; Luscombe, C. K. J. Am. Chem. Soc. 2009, 131, 12894.
23. Doubina, N.; Stoddard, M.; Bronstein, H.; Jen, A. K. Y.; Luscombe, C. K. Macromol. Chem. Phys. 2009, DOI: 10.1002/ macp.200900375.
24. Doubina, N.; Ho, A.; Jen, A. K. Y.; Luscombe, C. K. Macromolecules 2009, 42, 7670.
25. Smeets, A.; Van den Bergh, K.; De Winter, J.; Gergaux, P.; Verbiest, T.; Koeckelberghs, G. Macromolecules 2009, ASAP, DOI: 10.1021/ma901888h.
26. Beryozkina, T.; Senkovskyy, V.; Kaul, E.; Kiriy, A. Macromolecules 2008, 41, 7817.
27. Hidai, M.; Kashiwag, T.; Ikeuchi, T.; Uchida, Y. J. Organomet. Chem. 1971, 30, 279.
28. Loewe, R. S.; Ewbank, P. C.; Liu, J. S.; Zhai, L.; McCullough, R. D. Macromolecules 2001, 34,4324.
29. Masuda, N.; Tanba, S.; Sugie, A. Org. Lett. 2009,11,2297.
30. Lanni, E. L.; McNeil, A. J. J. Am. Chem. Soc. 2009, asap. DOI: 10.1021/ja904197q.
31. 31P NMR, we speculate that bithiophene formation is not prevented entirely in our case but does occur in a small amount not detectable by GC-MS.
32. Koeckelberghs, G.; Vangheluwe, M.; Samyn, C.; Persoons, A.; Verbiest, T. Macromolecules 2005, 38, 5554.
33. Vangheluwe, M.; Verbiest, T.; Koeckelberghs, G. Macromolecules 2008,41, 1041.
34. Miyakoshi, R.; Shimono, K.; Yokoyama, A.; Yokozawa, T. J. Am. Chem. Soc. 2006,128, 16012.
35. Yokoyama, A.; Kato, A.; Miyakoshi, R.; Yokozawa, T. Macromolecules 2008, 41,1211.
36. Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649.
37. Stefan, M. C.; Javier, A. E.; Osaka, I.; McCullough, R. D. Macromolecules 2009, 42, 30.
38. Huang, L.; Wu, S. P.; Qu, Y.; Geng, Y. H.; Wang, F. S. Macromolecules 2008, 41, 8944.