First synthesis of high molecular weight poly(2,6-difluoro-l,4-phenylene oxide) by oxidative polymerization

Macromolecules

Volumn 33, Issue 16, 2000, Pages 5766-5769

  Oyaizu, Kenichi ^a   Kumaki, Yousuke ^a   Saito, Kei ^a   Tsuchida, Eishun ^b  

^a WASEDA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHARGE TRANSFER; DIFFERENTIAL SCANNING CALORIMETRY; GLASS TRANSITION; MACROMOLECULES; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYPHENYLENE OXIDES; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

ELEMENTAL ANALYSIS; OXIDATIVE POLYMERIZATION; POLYDIFLUOROPHENYLENE OXIDE; THERMOLYSIS;

FLUORINE CONTAINING POLYMERS;

EID: 0034248244     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma000626+     Document Type: Article

References (42)

1. (a) Labadie, J. W.; Hedrick, J. L. Macromolecules 1990,23, 5371.
2. (b) Singh, R. Hay, A. S. Macromolecules 1991, 24, 2640.
3. Singh, R. Hay, A. S. Macromolecules 1992, 25, 1017.
4. Elce, E. Hay, A. S. J. Polym. Sci., Part A 1995, 33, 1143.
5. (e) Maier, G. Hecht, R.; Nuyken, O.; Burger, K.; Helmreich, B. Macromolecules 1993, 26, 2583.
6. Fluorophenol having an electron-donating 3-methyl-2-butenyl group polymerizes by the copper/pyridine-catalyzed oxidative coupling. Hyun, S. H.; Nishide, H.; Tsuchida, E.; Yamada, S. Polym. Bull. 1988, 19, 527.
7. Suatoni, J. C.; Snyder, R. E.; Clark, R. O. Anal. Chem. 1961, 33 1894
8. (a) Kubo, M. Itoh, Y.; Tsuji, M.; Oda, N.; Takeuchi, H.; Itoh, T. Macromolecules 1998, 31, 3469.
9. n = 1500) has been reported. Ikeda, R. Tanaka, H.; Uyama, H.; Kobayashi, S. Polym. Prepr. Jpn. Eng. Ed. 1999, 48, 541.
10. (a) Bioinorganic Catalysis, 2nd ed.; Reedijk, J. , Bouwman, E., Eds.; Marcel Dekker: New York, 1999.
11. (b) The Activation of Dioxygen and Homogeneous Catalysis; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993.
12. (a) Tsuchida, E. Yamamoto, K.; Miyatake, K.; Nishimura, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 2843.
13. (b) Yamamoto, K. Shouji, E.; Nishide, H.; Tsuchida, E. J. Am. Chem. Soc. 1993, 115, 5819.
14. Tsuchida, E. Yamamoto, K.; Oyaizu, K.; Suzuki, F.; Hay, A. S.; Wang, Z. Y. Macromolecules 1995, 28, 409.
15. Yamamoto, K; Tsuchida, E. Nishide, H.; Jikei, M.; Oyaizu, K. Macromotecules 1993, 26, 3432.
16. (a) Yamamoto, K. Oyaizu, K.; Tsuchida, E. J. Am. Chem. Soc. 1996, 118, 12665.
17. (b) Oyaizu, K. Tsuchida, E. J. Am. Chem. Soc. 1998, 120, 237.
18. Oyaizu, K. Yamamoto, K.; Yoneda, K; Tsuchida, E. Inorg. Chem. 1996, 35, 6634.
19. (a) Tsuchida, E. Oyaizu, K.; Dewi, E. L.; Imai, T.; Anson, F. C. Inorg. Chem. 1999, 38, 3704.
20. (b) Tsuchida, E. Yamamoto, K; Oyaizu, K.; Iwasaki, N.; Anson, F. C. Inorg. Chem. 1994, 33, 1056.
21. (a) Tolman, W. B. Ace. Chem. Res. 1997, 30, 227.
22. (b) Kitajima, N. Moro-oka, Y. Chem. Rev. 1994, 94, 737.
23. (a) Karlin, K. D.; Kaderli, S.; Zuberbuhler, A. D. Ace. Chem. Res. 1997, 30, 139.
24. (b) Kodera, M. Katayama, K; Tachi, Y.; Kano, K.; Hirota, S.; Fujinami, S.; Suzuki, M. J. Am. Chem. Soc. 1999, 121, 11006.
25. Enomoto, M. Aida, T. J. Am. Chem. Soc. 1999, 121, 874.
26. Halfen, J. A.; Mahapatra, S.; Wilkinson, E. C.; Kaderli, S.; Young, Jr., V. G.; Que, Jr., L.; Zuberbuhler, A. D.; Tolman, W. B. Science 1996, 271, 1397.
27. (a) Tyeklár, Z. Karlin, K. D. Ace. Chem. Res. 1989, 22, 241.
28. (b) Berreau, L. M.; Mahapatra, S.; Halfen, J. A.; Houser, R. P.; Young, Jr., V. G.; Tolman, W. B. Angew. Chem., Int. Ed. Engl. 1999, 38, 207.
29. Mahadevan, V. DuBois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. J. Am. Chem. Soc. 1999, 121, 5583.
30. Mahapatra, S. Halfen, J. A.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11575.
31. 2: C, 56.3; H, 1.57%. Found for THF soluble part: C, 55.4; H, 1.34%. Found for THF insoluble part: C, 55.7; H, 1.44%.
32. 19F NMR can be used to probe the electron density at the C2 atom (Figure 1). The low chemical shift indicates that the fluorine substituents would not be amenable to substitution with nucleophiles and that additional electronwithdrawing groups may be necessary to activate them by lowering the electron density at the site of nucleophilic reaction. Carter, K. R. Macromolecules 1995, 28, 6462.
33. Hay, A. S. J. Polym. Sci., Part A 1998, 36, 505.
34. Hay, A. S.; Dana, D. E. J. Polym. Sci., Part A 1989, 27, 873.
35. (a) Higashimura, H. Fujisawa, K; Moro-oka, Y.; Kubota, M.; Shiga, A.; Terahara, A.; Uyama, H.; Kobayashi, S. J. Am. Chem. Soc. 1998, 120, 8529.
36. (b) Higashimura, H. Kubota, M.; Shiga, A.; Fujisawa, K.; Moro-oka, Y.; Uyama, H.; Kobayashi, S. Macromolecules 2000, 33, 1986.
37. Hay, A. S.; Dana, D. E. Synthesis 1982, 2, 164.
38. 2PPO can be made into a transparent film which shows no X-ray diffraction peak.
39. Karasz, F. E.; Bair, H. E.; O'Reilly, J. M. J, Polym. Sci., Part A-2 1968, 6, 1141.
40. n = 4500) comparable with that of the previous study43 showed the onset of decomposition near 380 °C followed by a significant weight loss (15%).
41. A bis(μ-oxo)dicopper(III) complex has been isolated with l,4,7-tribenzyl-l,4,7-triazacyclononane as a ligand. Mahapatra, S. Halfen, J. A.; Wilkinson. E. C.: Pan. G.: Wang. X.; Young, Jr., V. G.; Cramer, C, J.; Que, Jr., L.; Tolman, W. B. J. Am.Chem. Soc. 1996, 118, 11555.
42. 9a