Synthesis, characterization, and thermal properties of ring-opening metathesis polynorbornenes and their hydrogenated derivatives bearing various ester and cyano groups

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 46, Issue 10, 2008, Pages 3314-3325

  Nishihara, Yasushi ^a   Izawa, Seisuke ^a   Inoue, Yoshiaki ^a   Nakayama, Yuushou ^b   Shiono, Takeshi ^b   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Kinetics (polym.); Living polymerization; Polyolefins; ROMP; Thermal properties

Indexed keywords

FUNCTIONAL GROUPS; LIVING POLYMERIZATION; POLYOLEFINS; RING OPENING POLYMERIZATION; THERMODYNAMIC PROPERTIES;

CYANO GROUPS; FUNCTIONALIZED POLAR NORBORNENES; RING-OPENING METATHESIS POLYMERIZATION (ROMP);

FUNCTIONAL POLYMERS;

EID: 43249107746     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.22671     Document Type: Article

References (107)

1. Ivin, K. J. Olefin Metathesis; Academic Press: London, 1983; pp 190-223.
2. Dragtan, V.; Balaban, A. T.; Dimonie, M. Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins; Wiley Interscience: New York, 1985; pp 155-185.
3. Buchmeiser, M. R. Chem Rev 2000, 100, 1565-1604.
4. Fürstner, A. Angew Chem Int Ed 2000, 39, 3012-3043.
5. Trnka, T. M.; Grubbs, R. H. Ace Chem Res 2001, 34, 18-29.
6. Slugovc, C. Macromol Rapid Commun 2004, 25, 1283-1297.
7. Katz, T. J. Angew Chem Int Ed 2005, 44, 3010-3019.
8. Schrodi, Y.; Pederson, R. L. Aldrichim Acta 2007, 40, 45-52.
9. Grubbs, R. H. Adv Synth Catal 2007, 349, 34-40.
10. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J Am Chem Soc 1992, 114, 3974-3975.
11. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J Am Chem Soc 1993, 115, 9856-9857.
12. Nguyen, S. T.; Grubbs, R. H. J Am Chem Soc 1993, 115, 9858-9859.
13. Wu, Z.; Benedicto, A. D.; Grubbs, R. H. Macromolecules 1993, 26, 4975-4977.
14. Schwab, P. E.; France, M. B.; Grubbs, R. H.; Ziller, J. W. Angew Chem Int Ed Engl 1995, 34, 2039-2041.
15. Kanaoka, S.; Grubbs, R. H. Macromolecules 1995, 28, 4707-4713.
16. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J Am Chem Soc 1996, 118, 100-110.
17. Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J Am Chem Soc 1996, 118, 784-790.
18. Wech, M.; Schwab, P.; Grubbs, R. H. Macromolecules 1996, 29, 1789-1793.
19. Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 3459-3469.
20. Week, M.; Mohr, B.; Maughon, B. R.; Grubbs, R. H. Macromolecules 1997, 30, 6430-6437.
21. Dias, E. L.; Grubbs, R. H. Organometallics 1998, 17, 2758-2767.
22. Maughon, B. R.; Morita, T.; Bielawski, C. W.; Grubbs, R. H. Macromolecules 2000, 33, 1929-1935.
23. Scherman, O. A.; Kim, H. M.; Grubbs, R. H. Macromolecules 2002, 35, 5366-5371.
24. Morita, T.; Maughon, B. R.; Bielawski, C. W.; Grubbs, R. H. Macromolecules 2000, 33, 6621-6623.
25. Hejl, A.; Scherman, O. A.; Grubbs, R. H. Macromolecules 2005, 38, 7214-7218.
26. Michelotti, F. W.; Keaveney, W. P. J Polym Sci Part A: Gen Pap 1965, 3, 895-905.
27. Rinehart, R. E.; Smith, H. P. J Polym Sci Part B: Polym Lett 1965, 3, 1049-1052.
28. Ast, W.; Rheinwald, G.; Kerber, R. Makromol Chem 1976, 177, 1349-1355.
29. Ivin, K. J.; Rooney, J. J.; Bencze, L.; Hamilton, J. G.; Lam, L. M.; Lapienis, G.; Reddy, B. S. R.; Ho, H. T. Pure Appl Chem 1982, 54, 447-460.
30. Schrock, R. R. Acc Chem Res 1990, 23, 158-165.
31. Schimetta, M.; Stelzer, F. Macromolecules 1994, 27, 3769-3772.
32. Heroguez, V.; Breunig, S.; Gnanou, Y.; Fontanille, M. Macromolecules 1996, 29, 4459-4464.
33. Perrott, M. G.; Novak, B. M. Macromolecules 1996, 29, 1817-1823.
34. Demonceau, A.; Stumpf, A. W.; Saive, E.; Noels, A. F. Macromolecules 1997, 30, 3127-3136.
35. Hayano, S.; Kurakata, H.; Tsunogae, Y.; Nakayama, Y.; Sato, Y.; Yasuda, H. Macromolecules 2003, 36, 7422-7431.
36. Nakayama, Y.; Tanimoto, M.; Shiono, T. Macromol Rapid Commun 2007, 28, 646-650.
37. Frenzel, U.; Nuyken, O. J Polym Sei Part A: Polym Chem 2002, 40, 2895-2916.
38. Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew Chem Int Ed Engl 2002, 41, 899-952.
39. Ilker, M. F.; Coughlin, E. B. Macromolecules 2002, 35, 54-58.
40. Quémener, D.; Héroguez, V.; Gnanou, Y. J Polym Sei Part A: Polym Chem 2006, 44, 2784-2793.
41. Liaw, D. J.; Huang, C. C.; Ju, J. Y. J Polym Sci Part A: Polym Chem 2006, 44, 3382-3392.
42. Liaw, D. J.; Huang, C. C.; Fu, C. W. J Polym Sci Part A: Polym Chem 2006, 44, 4428-4434.
43. Sutthasupa, S.; Terada, K.; Sanda, F.; Masuda, T. J Polym Sci Part A: Polym Chem 2006, 44, 5337-5343.
44. Gstrein, X.; Burtscher, D.; Szadkowska, A.; Barbasiewicz, M.; Stelzer, F.; Grela, K.; Slugovc, C. J Polym Sci Part A: Polym Chem 2007, 45, 3494-3500.
45. Sandholzer, M.; Fritz-Popovski, G.; Slugovc, C . J Polym Sci Part A: Polym Chem 2008, 46, 401-413.
46. Nakayama, Y.; Ikushima, N.; Ueyama, N.; Nakamura, A.; Harada, A. Chem Lett 2000, 434-435.
47. Takashima, Y.; Nakayama, Y.; Harada, A. Chem Lett 2001, 488-489.
48. Takashima, Y.; Nakayama, Y.; Yasuda, H.; Nakamura, A.; Harada, A. J Organomet Chem 2002, 654, 74-82.
49. Takashima, Y.; Nakayama, Y.; Yasuda, H.; Harada, A. J Organomet Chem 2002, 651, 114-123.
50. Hiya, K..; Nakayama, Y.; Yasuda, H. Macromolecules 2003, 36, 7916-7922.
51. Nakayama, Y.; Katsuda, K.; Yasuda, H. Polym J 2003, 35, 896-900.
52. Barrett, A. G. M.; Hopkins, B. T.; Koebberling, J. Chem Rev 2002, 102, 3301-3323.
53. Buchmeiser, M. R. New J Chem 2004, 28, 549557.
54. Pontrello, J. K.; Allen, M. J.; Underbakke, E. S.; Kiessling, L. L. J Am Chem Soc 2005, 127, 14536-14537.
55. Gibbs, J. M.; Park, S.-J.; Anderson, D. R.; Watson, K. J.; Mirkin, C. A.; Nguyen, S. T. J Am Chem Soc 2005, 127, 1170-1178.
56. Bertin, P. A.; Smith, D.; Nguyen, S. T. Chem Commun 2005, 3793-3795.
57. Ilker, M. F.; Nusslein, K.; Tew, G. N.; Coughlin, E. B. J Am Chem Soc 2004, 126, 15870-15875.
58. Wigglesworth, T. J.; Branda, N. R. Adv Mater 2004, 16, 123-125.
59. Stepp, B. R.; Nguyen, S. T. Macromolecules 2004, 37, 8222-8229.
60. Liaw, D. J.; Wang, K. L.; Lee, K. R.; Lai, J. Y. J Polym Sci Part A: Polym Chem 2007, 45, 3022-3031.
61. Sandholzer, M.; Lex, A.; Trimmel, G.; Saf, R.; Stelzer, F.; Slugovc, C. J Polym Sic Part A: Polym Chem 2007, 45, 1336-1348.
62. Park, J. W.; Lee, J. H.; Cho, H. N.; Choi, S. K. Macromolecules 1993, 26, 1191-1193.
63. Finkelshtein E. Sh.; Portnykh E. B.; Ushakov N. V.; Greengolts M. L.; Fedorova G. K.; Plate N. A. Macromol Rapid Commun 1994, 15, 155-159.
64. Breunig, S.; Risse, W. Makromol Chem 1992, 193, 2915-2927.
65. McLain, S. J.; McCord, E. F.; Arthur, S. D.; Hauptman, E.; Feldman, J.; Nugent, W. A.; Johnson, L. K.; Mecking, S.; Brookhart, M. Polym Mater Sci Eng 1997, 76, 246-247.
66. Bielawski, C. W.; Louie, J.; Grubbs, R. H. J Am Chem Soc 2000, 122, 12872-12873.
67. McManus, N. T.; Rempel, G. L. J Macromol Sci Rev Macromol Chem Phys 1995, C35, 239-285.
68. Sohn, B. H.; Gratt, J. A.; Lee, J. K.; Cohen, R. E. J Appl Polym Sci 1995, 58, 1041-1046.
69. Mashima, K.; Kaidzu, M.; Tanaka, Y.; Nakayama, Y.; Nakamura, A.; Hamilton, J. G.; Rooney, J. J. Organometallics 1998, 17, 4183-4195.
70. Kodemura, J.; Natsuume, T. Polym J 1995, 27, 1167-1172.
71. Kohara, T. Macromol Symp 1996, 101, 571-579.
72. Otsuki, T.; Goto, K.; Komiya, Z. J Polym Sci Part A: Polym Chem 2000, 38, 4661-1668.
73. Zheng, L.; Farris, R. J.; Coughlin, E. B. J Polym Sci Part A: Polym Chem 2001, 39, 2920-2928.
74. Ramakrishnan, S.; Berluche, E.; Chung, T. C. Macromolecules 1990, 23, 378-382.
75. Hillmyer, M. A.; Laredo, W. R.; Grubbs, R. H. Macromolecules 1995, 28, 6311-6316.
76. Incomplete combustion of the polymeric materials led to large deviations from the calculated value, especially for a fluorine atom. Thus, data of those elemental analyses were reported along with the percentage of ash residue.
77. Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew Chem Int Ed 2002, 41, 4035-1037.
78. Nishihara, Y.; Inoue, Y.; Itazaki, M.; Takagi, K. Org Lett 2005, 7, 2639-2641.
79. Nishihara, Y.; Inoue, Y.; Izawa, S.; Miyasaka, M.; Tanemura, K.; Nakajima, K.; Takagi, K. Tetrahedron 2006, 62, 9872-9882.
80. Ahmad, N.; Levison, J. J.; Bobinson, S. D.; Uttley, M. F. Inorg Synth 1974, 15, 45-64.
81. Nishihara, Y.; Inoue, Y.; Nakayama, Y.; Shiono, T.; Takagi, K. Macromolecules 2006, 39, 7458-7460.
82. Bielawski, C. W.; Grubbs, R. H. Angew Chem Int Ed 2000, 39, 2903-2906.
83. Fogg, D. E.; Foucault, H. M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, M. P., Eds.; Elsevier: Oxford, 2006; Vol. 11, p 18.
84. Nishihara, Y.; Inoue, Y.; Saito, A. T.; Nakayama, Y.; Shiono, T.; Takagi, K. Polym J 2007, 39, 318-329.
85. Slugovc, C.; Demel, S.; Stelzer, F. Chem Commun 2002, 2572-2573.
86. Slugovc, C.; Demel, S.; Riegler, S.; Hobisch, J.; Stelzer, F. J Mol Catal A: Chem 2004, 213, 107-113.
87. Riegler, S.; Demel, S.; Trimmel, G.; Slugovc, C.; Stelzer, F. J Mol Catal A: Chem 2006, 257, 53-58.
88. Choi, T.-L.; Grubbs, R. H. Angew Chem Int Ed 2003, 42, 1743-1746.
89. Matsumoto, S.; Komatsu, K.; Igarashi, K. Am Chem Soc Symp Ser 1977, 59, 303-317.
90. Miyamoto, Y.; Fujiki, M.; Nomura, K. J Polym Sei Part A: Polym Chem 2004, 42, 4248-4265.
91. Yoshida, Y.; Goto, K.; Komiya, Z. J Appl Polym Sei 1997, 66, 367-375.
92. Yoshida, Y.; Yoshinari, M.; Iko, A.; Komiya, Z. Polym J 1998, 30, 819-823.
93. Liaw, D.-J.; Tsai, C.-H. J Mol Catal A: Chem 1999, 147, 23-31.
94. Liaw, D.-J.; Tsai, C.-H. Polymer 2000, 41, 2773-2780.
95. Gibson, V. C.; Okada, T. Macromolecules 2000, 33, 655-656.
96. Rachapudy, H.; Smith, G. G.; Raju, V. R.; Graessley, W. W. J Polym Sci Polym Phys Ed 1979, 17, 1211-1222.
97. Drouin, S. D.; Yap, G. P. A.; Fogg, D. E. Inorg Chem 2000, 39, 5412-5414.
98. Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 3196-3201.
99. Drouin, S. D.; Zamanian, F.; Fogg, D. E. Organometallics 2001, 20, 5495-5497.
100. Fogg, D. E.; Amoroso, D.; Drouin, S. D.; Snelgrove, J.; Conrad, J.; Zamanian, F. J Mol Catal A: Chem 2002, 190, 177-184.
101. Nkosi, B. S.; Coville, H. J.; Albers, M. O.; Gordon, C.; Viney, M.; Singleton, E. J Organomet Chem 1990, 386, 111-119.
102. Zanetti, N. C.; Spindler, F.; Spencer, J.; Togni, A.; Rihs, G. Organometallics 1996, 15, 860-866.
103. Bianchini, C.; Barbaro, P.; Scapacci, G.; Zanobini, F. Organometallics 2000, 19, 2450-2461.
104. Yang, H.; Islam, M.; Budde, C.; Rowan, S. J. J Polym Sei Part A: Polym Chem 2003, 41, 21072116.
105. Sworen, J. C.; Smith, J. A.; Berg, J. M.; Wagener, K. B. J Am Chem Soc 2004, 126, 11238-11246.
106. Dettmer, C. M.; Gray, M. K.; Torkelson, J. M.; Nguyen, S. T. Macromolecules 2004, 37, 5504-5506.
107. Kamakshi, R.; Reddy, B. S. R. J Polym Sci Part A: Polym Chem 2008, 46, 1521-1531.