Synthesis of well-defined polythiophene with oxyethylene side chain: Effect of phosphine ligands on catalyst-transfer polycondensation

Macromolecules

Volumn 39, Issue 23, 2006, Pages 7793-7795

  Adachi, Isao ^a   Miyakoshi, Ryo ^a   Yokoyama, Akihiro ^a   Yokozawa, Tsutomu ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; POLYCONDENSATION; SYNTHESIS (CHEMICAL);

EXCHANGE REACTION; LASER DESORPTION IONIZATION; LIGANDS; PHOSPHINE; SODIUM TRIFLUOROACETATE;

ORGANIC COMPOUNDS;

EID: 33845238042     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma061809k     Document Type: Article

References (21)

1. The first report of organometallic polycondensation for the synthesis of poly(3-alkylthiophene): Yamamoto, T.; Sanechika, K. Chem. Ind. 1982, 301-302.
2. (a) McCullough, R. D.; Lowe, R. D. J. Chem. Soc., Chem. Commun. 1992, 70-72.
3. (b) McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904-912.
4. (a) Chen, T.-A.; Rieke, R. D. J. Am. Chem. Soc. 1992, 114, 10087-10088.
5. (b) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233-244.
6. (a) Yokoyama, A.; Miyakoshi, R.; Yokozawa, T. Macromolecules 2004, 37, 1169-1171.
7. (b) Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Macromol. Rapid Commun. 2004, 25, 1663-1666.
8. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. J. Am. Chem. Soc. 2005, 127, 17542-17547.
9. McCullough and co-workers have also reported the chain-growth polymerization nature of the Ni-catalyzed polymerization for the synthesis of poly(3-alkylthiophene): (a) Sheina, E. E.; Liu, J.; Iovu, M. C.; Laird, D. W.; McCullough, R. D. Macromolecules 2004, 37, 3526-3528.
10. (b) Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649-8656.
11. Bryce, M. R.; Chissel, A.; Kathirgamanathan, P.; Parker, D.; Smith, N. R. M. J. Chem. Soc., Chem. Commun. 1987, 466-467.
12. (a) McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608-11609.
13. (b) Sheina, E. E.; Khersonsky, S. M.; Jones, E. G.; McCullough, R. D. Chem. Mater. 2005, 17, 3317-3319.
14. (a) Marsella, M. J.; Swager, T. M. J. Am. Chem. Soc. 1993, 115, 12214-12215.
15. (b) Marsella, M. J.; Carroll, P. J.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 9832-9841.
16. Yamamoto, T.; Omote, M.; Miyazaki, Y.; Kashiwazaki, A.; Lee, B.-L.; Kanbara, T.; Osakada, K.; Inoue, T.; Kubota, K. Macromolecules 1997, 30, 7158-7165.
17. van Beek, R.; Jenneskens, L. W.; Zdravkova, A. N.; van der Eerden, J. P. J. M.; van Walree, C. A. Macromol. Chem. Phys. 2005, 206, 1006-1014.
18. Loewe, R. S.; Ewbank, P. C.; Liu, J.; Zhai, L.; McCullough, R. D. Macromolecules 2001, 34, 4324-4333.
19. The selective formation of 1 by the reaction of 2 with isopropyl-magnesium chloride was confirmed by the detection of 2-bromo-3-[2-(2-methoxyethoxy)ethoxy]methylthiophene after hydrolysis of a small aliquot of the reaction mixture before addition of the Ni catalyst. The conversion of 2 to 1 was 89-99% determined by GC, and remaining 2 was recovered after the polymerization.
20. GPC profiles are shown in the Supporting Information.
21. + adducts, and the apparent deviation is caused by overlap with the peaks of fragmented Br/H end polymers.