Effect of diene ligands in the rhodium-catalyzed polymerization of phenylacetylene

Macromolecules

Volumn 39, Issue 26, 2006, Pages 8977-8981

  Saeed, Irfan ^a   Shiotsuki, Masashi ^a   Masuda, Toshio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYSIS; COORDINATION REACTIONS; MOLECULAR STRUCTURE; MONOMERS; RHODIUM;

DIENE LIGANDS; PHENYLACETYLENE; POLYMER YIELD;

OLEFINS;

EID: 33846204663     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma061689g     Document Type: Article

References (68)

1. Buchmeiser, M. R. Adv. Polym. Sci. 2005, 176, 89-119.
2. Mayershofer, M. G.; Nuyken, O. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5723-5747.
3. Masuda, T.; Sanda, F. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 3, pp 375-406.
4. Masuda, T. Polymeric Material Encyclopedia; Salamone, J. C, Ed.; CRC Press: Boca Raton, FL, 1996, p 32.
5. Mayershofer, M. G.; Nuyken, O.; Buchmeiser, M. R. Macromolecules 2006, 39, 3484-3493.
6. Katsumata, T.; Shiotsuki, M.; Masuda, T. Macromol. Chem. Phys. 2006, 207, 1244-1252.
7. Katsumata, T.; Shiotsuki, M.; Kuroki, S.; Ando, I.; Masuda, T. Polym. J. 2005, 37, 608-616.
8. Zhang, Y.; Wang, D.; Wurst, K.; Buchmeiser, M. R. J. Organomet. Chem. 2005, 690, 5728-5735.
9. Krause, J. O.; Nuyken, O.; Buchmeiser, M. R. Chem.-Eur. J. 2004, 10, 2029-2035.
10. Krause, J. O.; Zarka, M, T.; Anders, U.; Weberskirch, R.; Nuyken, O.; Buchmeiser, M. R. Angew. Chem., Int. Ed. 2003, 42, 5965-5969.
11. Li, K.; Wei, G.; Pollack, S. K. Macromolecules 2002, 35, 4573-4576.
12. Zhang, X.; Yang, M.; Sun, H. J. Mol. Catal., A: Chem. 2001, 169, 63-66.
13. Zhang, X.; Yang, M. J. Mol. Catal., A: Chem. 2001, 169, 27-31.
14. Wang, R.; Belanger-Gariepy, F.; Zargarian, D. Organometallics 1999, 18, 5548-5552.
15. Sedlacek. J.; Vohlidal, J. Collect. Czech. Chem. Commun. 2003, 68, 1745-1790.
16. Tang, B. Z.; Lam, J. W. Y. Acc. Chem. Res. 2005, 38, 745-754.
17. Bredas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971-5004.
18. Tang, B. Z.; Lam, J. W. Y. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2607-2629.
19. Nagai, K.; Masuda, T.; Nakagawa, T.; Freeman, B. D.; Pinnau, I. Prog. Polym. Sci. 2001, 26, 721-798.
20. Harrel, K. J. S.; Nguyen, S. T. In Handbook of Advanced Electronic and Photonic Material and Devices; Nalwa, H. S., Ed.; Academic: San Diego, 2001; Vol. 8, Chapter 3, p 131.
21. Shirakawa, H. Angew. Chem., Int. Ed. 2001, 40, 2574-2580.
22. MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590.
23. Heeger, A. J. Angew. Chem., Int. Ed. 2001, 40, 2591-2611.
24. Choi, S.-K.; Gal, Y.-S.; Jin, S.-H.; Kim, H. K. Chem. Rev. 2000, 100, 1645-1682.
25. Furlani, A.; Napoletano, C.; Russo, M. V., Camus, A.; Marsich, N. J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 75-86.
26. Furlani, A.; Napoletano, C.; Russo, M. V.; Feast, W. J. Polym. Bull. 1986, 16, 311-317.
27. Tabata, M.; Sone, T.; Sadahiro, Y. Macromol. Chem. Phys. 1999, 200, 265-282.
28. Tabata, M.; Yang, W.; Yokota, K. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 1113-1120.
29. Tabata, M.; Yang, W.; Yokota, K. Polym. J. 1990, 22, 1105-1107.
30. Mastrorilli, P.; Nobile, C. F.; Gallo, V.; Suranna, G. P.; Farinola, G. J. Mol. Catal., A: Chem. 2002, 184, 73-78.
31. Tang, B. Z.; Poon, W. H.; Leung, S. M.; Leung, W. H.; Peng, H. Macromolecules 1997, 30, 2209-2212.
32. Kishimoto, Y.; Itou, M.; Miyatake, Y.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662-6666.
33. Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012.
34. Kozuka, M.; Sone, T.; Sadahiro, Y.; Tabata, M.; Enoto, T. Macromol. Chem. Phys. 2002, 203, 66-70.
35. Tabata, M.; Inaba, Y.; Yokota, K.; Nozaki, Y. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 465-475.
36. Nakako, H.; Nomura, R.; Masuda, T. Macromolecules 2001, 34, 1496-1502.
37. Nakako, H.; Mayahara, Y.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 2000, 33, 3978-3982.
38. Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836.
39. Nakako, H.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 1999, 32, 2861-2864.
40. Tabei, J.; Shiotsuki, M.; Sanda, F.; Masuda, T. Macromolecules 2005, 38, 5860-5867.
41. Tabei, J.; Nomura, R.; Masuda, T. Macromolecules 2003, 36, 573-577.
42. Nomura, R.; Tabei, J.; Masuda, T. Macromolecules 2002, 35, 2955-2961.
43. Tabei, J.; Nomura, R.; Masuda, T. Macromolecules 2002, 35, 5405-5409.
44. Nomura, R.; Tabei, J.; Masuda, T. J. Am. Chem. Soc. 2001, 123, 8430-8431.
45. Teraguchi, M.; Masuda, T. Macromolecules 2000, 33, 240-242.
46. Mitsuyama, M.; Ishii, R.; Kondo, K. J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 3419-3427.
47. Goto, H.; Akagi, H.; Shirakawa, H. Synth. Met. 1997, 84, 373-374.
48. Dulog, L.; Lutz, S. Macromol. Chem., Rapid Commun. 1995, 16, 43-45.
49. Miura, Y.; Matsumoto, M.; Ushitani, Y. Macromolecules 1993, 26, 2628-2630.
50. Fujii, A.; Ishida, T.; Koga, N.; Iwamura, H. Macromolecules 1991, 24, 1077-1082.
51. Baghurst, D. R.; Michael, D.; Mingos, P.; Watson, M. J. J. Organomet. Chem. 1989, 368, 43-45.
52. Brewer, J. P. N.; Eckhard, I. F.; Heaney, H.; Marplies, B. A. J. Chem. Soc. C 1968, 6, 664-676.
53. Heaney, H.; Jablonski, J. M. J. Chem. Soc. C 1968, 15, 1895-1898.
54. Bennett, M. A.; McMahon, I. J.; Felling, S.; Robertson, G. B.; Wickramasinghe, W. A. Organometallics 1985, 4, 754-761.
55. Roe, D. M.; Massey, A. G. J. Organomet. Chem. 1971, 28, 273-279.
56. 9Li, etc.), it can polymerize phenylacetylene in appreciable yield (50-60%) to afford polymer with a molecular weight on the order of 104.
57. Monodentate olefins, ethylene and cyclooctene, and bidentate oleflns, such as 1,3-butadiene, 1,4-cyclohexadiene, 1,4-benzoquinone, tetramethyl-1,4-benzoquinone, hexachloro-1,3-cyclopentadiene, hexachloronorbornadiene-l,2-dicarboxylic acid dimethyl ester, tetraphenylcy-clopentadienone, and 1,3,5,7-cyclooctatertraene, were hardly effective to induce polymerization of substituted acetylenes.
58. Kanki, K.; Misumi, Y.; Masuda, T. Macromolecules 1999, 32, 2384-2386.
59. Saeed, I.; Shiotsuki, M.; Masuda, T. Macromolecules 2006, 39, 5347-5351.
60. Zhao, P.; Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 12066-12073.
61. An exception to this generally observed trend has been reported: Saeed, I.; Shiotsuki, M.; Masuda, T. J. Mol. Catal., A: Chem. 2006, 254, 124-130.
62. An exception to this generally observed trend has been reported: Katayama, H.; Yamamura, K.; Miyaki, Y.; Ozawa, F. Organometallics 1997, 16, 4497-5000.
63. Stoebenau, E. J.; Jordan, R. F. J. Am. Chem. Soc. 2006, 128, 8162-8175.
64. Hartley, F. R. Angew. Chem., Int. Ed. Engl. 1972, 11, 596-606.
65. Chatt, J.; Duncanson, L. J. J. Chem. Soc. 1953, 2939-2947.
66. Dewar, M. J. S. Bull. Soc. Chim. Fr. 1951, 18, C71-79.
67. Cotton, F. A.; Wilkinson, G. In Advanced Inorganic Chemistry, 4th ed.; John Wiley & Sons: New York, 1980; p 1049.
68. b). For more details, see ref 15.