Chain-growth polymerization for the synthesis of polyfluorene via Suzuki Miyaura coupling reaction from an externally added initiator unit

Journal of the American Chemical Society

Volumn 129, Issue 23, 2007, Pages 7236-7237

  Yokoyama, Akihiro ^a   Suzuki, Hirofumi ^a   Kubota, Yasuhiro ^b   Ohuchi, Kazuei ^b   Higashimura, Hideyuki ^b   Yokozawa, Tsutomu ^a  

^a KANAGAWA UNIVERSITY   (Japan)

^b SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (7 BROMO 9,9 DIOTYL 9H FLUOREN 2 YL) 4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLANE; 4 BROMO 2,5 DIBUTYLOXYBENZENE BORIC ACID; BORON DERIVATIVE; FLUORENE; HALIDE; MONOMER; NICKEL; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONJUGATION; GRIGNARD REACTION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; POLYMERIZATION; SUZUKI REACTION; SYNTHESIS;

EID: 34250840712     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070313v     Document Type: Article

References (26)

1. For a review, see: Yamamoto, T. Macromol. Rapid Commun. 2002, 23, 583.
2. (a) Yokoyama, A.; Miyakoshi, R.; Yokozawa, T. Macromolecules 2004, 37, 1169. (b) Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Macromol. Rapid Commun. 2004, 25, 1663.
3. (c) Adachi, I.; Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. Macromolecules 2006, 39, 7793.
4. McCullough and co-workers have also reported the chain-growth polymerization of Grignard-type thiophene monomers: (a) Sheina, E. E.; Liu, J.; Iovu, M. C.; Laird, D. W.; McCullough, R. D. Macromolecules 2004, 37, 3526.
5. (b) Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649.
6. Miyakoshi, R.; Shimono, K.; Yokoyama, A.; Yokozawa, T. J. Am. Chem. Soc. 2006, 128, 16012.
7. Miyakoshi, R.; Yokoyama, A.; Yokozawa, T. J. Am. Chem. Soc. 2005, 127, 17542.
8. For an example of a surface grafting polyfluorene synthesized by step-growth polymerization, see: Beinhoff, M.; Appapillai, A. T.; Underwood, L. D.; Frommer, J. E.; Carter, K. R. Langmuir 2006, 22, 2411.
9. Stambuli, J. P.; Incarvito, C. D.; Buhl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184.
10. Vahlenkamp, T.; Wegner, G. Macromol. Chem. Phys. 1994, 195, 1933.
11. (a) Marsitzky, D.; Klapper, M.; Mullen, K. Macromolecules 1999, 32, 8685.
12. (b) Johansson, D. M.; Theander, M.; Granlund, T.; Inganas, O.; Andersson, M. R. Macromolecules 2001, 34, 1981.
13. (c) Sandee, A. J.; Williams, C. K.; Evans, N. R.; Davies, J. E.; Boothby, C. E.; Kohler, A.; Friend, R. H.; Holmes, A. B. J. Am. Chem. Soc. 2004, 126, 7041.
14. (d) Wu, Y.; Li, J.; Fu, Y.; Bo, Z. Org. Lett. 2004, 6, 3485.
15. (e) Li, B.; Xu, X.; Sun, M.; Fu, Y.; Yu, G.; Bo, Z. Macromolecules 2006, 39, 456.
16. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
17. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
18. (a) Sinclair, D.; Sherburn, M. S. J. Org. Chem. 2005, 70, 3730.
19. (b) Dong, C.-G.; Hu, Q.-S. J. Am. Chem. Soc. 2005, 127, 10006.
20. (c) Weber, S. K.; Galbrecht, F.; Scherf, U. Org. Lett. 2006, 8, 4039.
21. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
22. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
23. For a review, see: Neher, D. Macromol. Rapid Commun. 2001, 22, 1365.
24. See Supporting Information for details.
25. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc 2003, 125, 13944.
26. n = 1.51) was broad. This appeared to be due to precipitation of the growing polymer at the late stage of the polymerization.