Ring-Opening Metathesis Polymerization (ROMP) and Related Processes

Materials Science and Technology: A Comprehensive Treatment

Volumn , Issue , 2008, Pages 65-104

  Grubbs, Robert H ^a   Khosravi, Ezat ^b  

^a California Institute of Technology   (United States)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Heterogeneous mixtures; Metal carbene; Polymerizations; Ring opening metathesis polymerization; Rotamer isomerization

Indexed keywords

CONDENSED MATTER PHYSICS; MATERIALS SCIENCE; POLYMERIZATION;

HETEROGENEOUS MIXTURES; METAL CARBENES; RING OPENING METATHESIS POLYMERIZATION; ROTAMERS;

RING OPENING POLYMERIZATION;

EID: 84953790944     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619313.ch3     Document Type: Chapter

References (162)

1. Bazan, G. C. (1990), Ph. D. Thesis, Massachusetts Institute of Technology, U. S. A.
2. Bazan, G., Albagli, D., unpublished.
3. Bazan, G. C., Schrock, R. R. (1991), Macromolecules 24, 817.
4. Bazan, G., Schrock, R. R., Khosravi, E., Feast, W. J., Gibson, V. C. (1989) Polym. Commun. 30, 258.
5. Bazan, G., Schrock, R. R., Khosravi, E., Feast, W. J., Gibson, V. C., O'Regan, M. B., Thomas, J. K., Davis, W. M. (1990), J. Am. Chem. Soc. 112, 8387.
6. Bazan, G. C., Schrock, R. R., Cho, H., Gibson, V. C. (1991a), Macromolecules 24, 4495.
7. Bazan, G. C., Oskam, J. H., Cho, H. N., Park, L. Y., Schrock, R. R. (1991b), J. Am. Chem. Soc. 113, 6899.
8. Bazan, G. C., Renak, M. L., Sun, B. J. (1996), Macromolecules 29, 1085.
9. Benedicto, A. D., Novak, B. M., Grubbs, R. H. (1992), Macromolecules 25, 5893.
10. Berets, D. J., Smith, D. S. (1968), Trans. Faraday Soc. 64, 823.
11. Blonsky, P. M., Shriver, D. F., Austin, P., Allcock, H. R. (1984), J. Am. Chem. Soc. 106, 6854.
12. Bott, D. C., Brown, C. S., Feast, W. J., Parker, D., Winter, J. N. (1985), Mol. Cryst. Liq. Cryst. 117, 9.
13. Bott, D. C., Brown, C. S., Chai, C. K., Walker, N. S., Feast, W. J., Foot, P. J. S., Calvert, P. D., Billing-ham, N. C., Friend, R. H. (1986), Synth. Met. 14, 245.
14. Breunig, S., Heroguez, V., Gnanou, Y., Fontanille, M. (1995), Macromol. Symp. 95, 151.
15. Broeders, Y., Feast, W. J., Gibson, V. C., Khosravi, E. (1996), J. Chem. Soc., Chem. Commun. 343.
16. Brown-Wensley, A. K., Buchwald, S. L., Cannizzo, L., Clawson, L., Ho, S., Meinhardt, D., Stille, J. R., Straus, D., Grubbs, R. H. (1983), Pure Appl. Chem. 55, 1733.
17. Burroughes, J. H., Bradley, D. D. C., Brown, A. R., Marks, R. N., Friend, R. H., Burn, P. L., Holms, A. B. (1990), Nature 347, 539.
18. Cannizzo, L. F., Grubbs, R. H. (1987), Macromolecules 20, 1488.
19. Cannizzo, L. F., Grubbs, R. H., (1988), Macromolecules 21, 1961.
20. Chien, J. C. W. (1984), in: Polyacetylene Chemistry, Physics and Material Science, New York: Academic;
21. Skotheim, T. A. (1986), Handbook of Conducting Polymers, New York: Marcel Dekker.
22. Coates, G. W., Waymouth. R. M. (1995) Science 267, 217.
23. Coles, H. J., Simon. R. (1985), in: Recent Advances in Liquid Crystalline Polymers: Chapoy, L. L. (Ed.). New York: Elsevier Applied Science, Chap. 22.
24. Conticello, V. P., Gin, D. L., Grubbs. R. H. (1992), J. Am. Chem. Soc. 114, 9708.
25. Crowe, W. E.. Gibson, V. C., Mitchell, J. P., Schrock, R. R. (1990), Macromolecules 23, 3534.
26. Cummins, C. C., Beachy, M. D., Schrock, R. R, Vale, M. G., Sankaran, V., Cohen, R. E. (1991), Chem. Mater. 3, 1153.
27. Cummins, C. C., Schrock, R. R., Cohen. R. E. (1992), Chem. Mater. 4, 27.
28. Davies, G. R. (1981), in: Physics of Dielectric Solids (Inst. Phys. Conf. Ser. No. 58). Bristol: Institute of Physics, p. 50.
29. Davies, G. R., Feast, W. J., Gibson, V. C., Hubbard, H. V. A., Khosravi, E., Petty, M., Petty, M. C., Ward, I. M., Wellings, S. C. (1992), Proc. Symp. Functionele Polymeren-de Polymeren van Morgen, TU Delft: Delft, Netherlands.
30. Davies. G. R., Hubbard, H. V. A., Ward, I. M., Marshall. E. L., Gibson, V. C., Khosravi. E., Feast, W. J. (1995). Polymer 36, 235.
31. Dounis, P. (1994), Ph. D. Thesis, Durham University, U. K.
32. Draughton. V. Balaban, A. T., Dimonic, M. (1995), Olefin Metathesis and Ring Opening Polymerisation of Cyclo Olefins, 2nd ed. New York: Wiley Interscience.
33. Edwards, J. H., Feast, W. J., Bott, D. C. (1984), Polymer 25, 395.
34. El-Saafin. I. F. A. F., Feast, W. J. (1982), J. Mol. Catal. 15, 61.
35. Feast, W. J., Harrison, D. B. (1991), J. Mol. Catal. 65, 63.
36. Feast, W. J., Winter, J. N. (1985), J. Chem. Soc., Chem. Commun., 202.
37. Feast, W. J., Gibson, V. C., Marshall, E. L. (1992a), J. Chem. Soc., Chem. Commun., 1157.
38. Feast, W. J., Gibson, V. C., Ivin, K. J., Khosravi, E., Kenwright. A. M., Marshall, E. L., Mitchell, J. P. (1992b). Makromol. Chem. Chem. Phys. 193, 2103.
39. Feast, W. J., Gibson, V. C., Ivin, K. J., Kenwright, A. M., Khosravi, E. (1994a), J. Chem. Soc., Chem. Commun., 1399.
40. Feast, W. J., Gibson, V. C., Khosravi, E., Marshall, E. L. (1994b), J. Chem. Soc., Chem. Commun., 9.
41. Feast, W. J., Gibson, V. C., Johnson, A. F., Khosravi, E., Mohsin, M. A. (1994c). Polymer 35, 354.
42. Feast, W. J., Gibson, V. C., Khosravi, E., Marshall, E. L., Wilson, B. (1995), Ziegler Catalysts, Recent Scientific Innovations and Technical Improvements. Fink. G., Mulhaupt, R., Brintzinger, M. M. (Eds.). Berlin: Springer, 469.
43. Feast, W. J. Gibson, V. C., Johnson, A. F., Khosravi, E., Mohsin, M. A. (1997), J. Mol. Catal., A: Chem. 115, 37.
44. Feldman, J., Schrock, R. R. (1991), Prog. Inorg. Chem. 39, 1.
45. Finkelmann, H., Ringsdorf, H., Wendroff, J. H. (1978a), Makromol. Chem. 179, 273.
46. Finkelmann, H., Happ, M., Portugall, M., Ringsdorf, H. (1978b), Makromol. Chem. 179, 2541.
47. Finkelmann, H., Keichle, U., Rehage, G. (1983), Mol. Cryst. Liq. Cryst. 94, 3453.
48. Fox, H. H., Yap, K. B., Robbins, J., Cai, S., Schrock, R. R. (1992), Inorg. Chem. 31, 2287.
49. Fox, H. H., Lee, J. K., Park, L. Y., Schrock, R. R. (1993), Organometallics 12, 759.
50. France, M. B., Paciello, R. A., Grubbs, R. H. (1993a), Macromolecules 26, 4739.
51. France, M. B., Grubbs, R. H., McGrath, D. V., Benedicto, A. D. (1993b), Macromolecules 26, 4742.
52. Fu, G. C., Grubbs, R. H. (1992a), J. Am. Chem. Soc 114, 5426.
53. Fu, G. C., Grubbs, R. H. (1992b), J. Am. Chem. Soc. 114, 7324.
54. Fu, G. C., Nguyen, S. T., Grubbs, R. H. (1993), J. Am. Chem. Soc. 115, 9856.
55. Gilliom, L. R., Grubbs, R. H. (1986), J. Am. Chem. Soc. 108, 733.
56. Ginsburg, E. J., Gorman, C. B., Marder, S. R., Grubbs, R. H. (1989), J. Am Chem. Soc. 111, 7621.
57. Gorman, C. B., Ginsburg, E. J., Grubbs, R. H. (1993), J. Am. Chem. Soc. 115, 1397.
58. Grubbs, R. H., Pine, S. H. (1991), in: Comprehensive Organic Synthesis. Vol. 5: Trost, B. M. (Ed.). New York: Pergamon, Chap. 9.3.
59. Grubbs, R. H., Tumas, W. (1989), Science 243, 907.
60. Grubbs, R. H., Johnson, L. K., Nguyen, S. T. (1994), Patent Nos. 5,312,940 and 5,342,909.
61. Grubbs, R. H., Miller, S. J., Fu, G. C. (1995), Acc. Chem. Res. 28, 446.
62. Heroguez, V., Gnanou, Y., Fontanille, M. (1996a), Macromol. Rapid. Commun. 17, 137.
63. Heroguez, V., Breunig, S., Gnanou, Y., Fontanille, M. (1996b), Macromolecules 29, 4459.
64. Hillmyer, M. A., Grubbs, R. H. (1993), Macromolecules 26, 872.
65. Hillmyer, M. A., Lepetit, C., McGrath, D. V., Novak, B. M., Grubbs, R. H. (1992), Macromolecules 25, 3345.
66. Hillmyer, M. A., Nguyen, S. T., Grubbs, R. H. (1997), Macromolecules 30, 718.
67. Ivin, K. J. (1983), Olefin Metathesis. London: Academic.
68. Jozefiak, T. H., Ginsburg, E. J., Gorman, C. B., Grubbs, R. H., Lewis, N. S. (1993), J. Am. Chem. Soc. 115, 4705.
69. Kahlert, H., Leising, G. (1985), Mol. Cryst. Liq. Cryst. 117, 1.
70. Karlen, T., Ludi, A., Muhlebach, A., Bernhard, P., Pharisa, C. (1995), J. Polym. Sci., Part A: Polym.
71. Chem. 33, 1665; Hafner, A., Van der Schaaf, P. A., Muhlebach, A. (1996), Chimia 50, 131.
72. Klavetter, F. L., Grubbs, R. H. (1988), J. Am Chem. Soc. 110, 7807.
73. Knoll, K., Schrock, R. R. (1989), J. Am. Chem. Soc. 111, 7989.
74. Knoll, K., Krouse, S. A., Schrock, R. R. (1988), J. Am. Chem. Soc. 110, 4424.
75. Komiya, Z., Schrock, R. R. (1993a), Macromolecules 26, 1387.
76. Komiya, Z., Schrock, R. R. (1993b), Macromolecules 26, 1393.
77. Komiya, Z., Pugh, C., Schrock, R. R. (1992a), Macromolecules 25, 3609.
78. Komiya, Z., Pugh, C., Schrock, R. R. (1992b), Macromolecules 25, 6586.
79. Kress, J., Osborn, J. A. (1983), J. Am. Chem. Soc. 105, 6346.
80. Kress, J., Osborn, J. A. (1987), J. Am. Chem. Soc. 109, 3953.
81. Kress, J., Wesolek, M., Osborn, J. A. (1982), J. Chem. Soc, Chem. Commun., 514.
82. Kress, J., Agyero, A., Osborn, J. A. (1986), J. Mol. Catal. 36, 1.
83. Krouse, S. A., Schrock, R. R. (1988), Macromolecules 21, 1885.
84. Kyba, E. P., Helgeson, R. C., Madan, K., Gokel, G. W., Tarnowski, T. L., Moore, S. S., Cram, D. J. (1977), J. Am. Chem. Soc. 99, 2564.
85. Lundberg, R. D., Bailey, F. E., Callard, R. W. (1966), J. Polym. Sci. A-14, 1563.
86. Lynn, D. M., Kanaoka, S., Grubbs, R. H. (1996), J. Am. Chem. Soc. 118, 784.
87. Lynn, D. M., Mohr, B., Minoda, M., Grubbs, R. H. (1997), J. Am. Chem. Soc., unpublished.
88. Manning, D. D., Hu, X., Beck, P., Kiessling, L. L. (1997), J. Am. Chem. Soc. 119, 3161.
89. Maughon, B. R., Grubbs, R. R. (1996), Macromolecules 29, 5765.
90. Maughon, B. R., Weck, M., Mohr, B., Grubbs, R. H. (1997), Macromolecules 30, 257.
91. McConville, D. H., Wolf, J. R., Schrock, R. R. (1993), J. Am. Chem. Soc. 115, 4413.
92. Miao, Y.-J., Bazan, G. C. (1994a), J. Am. Chem. Soc. 116, 9379.
93. Miao, Y.-J., Bazan, G. C. (1994b), Macromolecules 27, 1063.
94. Michelotti, F. W., Carter, J. H. (1965), Polym. Prepr. 6 (1), 224.
95. Michelotti, F. W., Keaveney, W. P. (1965), J. Polym. Sci. A3, 3, 895.
96. Mitchell, J. P. (1991), Ph. D. Thesis, Durham University, U. K.
97. Mitchell, J. P., Gibson, V. C., Schrock, R. R. (1991), Macromolecules 24, 1220.
98. Mohr, B., Lynn, D. M., Grubbs, R. H. (1996), Organometallics 15, 4317.
99. Montaner, A., Rolland, M., Sauvagol, J. L., Galtier, M., Almairac, R., Ribet, J. L. (1988), Polymer 29, 1101.
100. Nakamura, S., Hirao, A. (1990), Progr. Polym. Sci. 15, 229.
101. Ng Cheong Chan, Y., Schrock, R. R. (1993), Chem. Mater. 5, 566.
102. Ng Cheong Chan, Y., Craig, G. S. W., Schrock, R. R., Cohen, R. E. (1992a), Chem. Mater. 4, 885.
103. Ng Cheong Chan, Y., Schrock, R. R., Cohen, R. E. (1992b), Chem. Mater. 4, 24.
104. Nguyen, S.-B. T., Grubbs, R. H. (1993), J. Am. Chem. Soc. 115, 9858.
105. Nguyen, S.-B. T., Johnson, L. K., Grubbs, R. H. (1992), J. Am. Chem. Soc. 114, 3974.
106. Novak, B. M., Grubbs, R. H. (1988a), J. Am. Chem. Soc. 110, 960.
107. Novak, B. M., Grubbs, R. H. (1988b), J. Am. Chem. Soc. 110, 7542.
108. Novak, B. M., Risse, W., Grubbs, R. H. (1992), Adv. Polym. Sci. 102, 47.
109. O'Dell, R., McConville, D. H., Hogmeister, G. E., Schrock, R. R. (1994), J. Am. Chem. Soc 116, 3414.
110. Ofer, D., Park, L. Y., Schrock, R. R., Wrighton, M. S. (1991), Chem. Mater. 3, 573.
111. Oskam, J. H., Schrock, R. R. (1992), J. Am. Chem. Soc. 114, 7588.
112. Oskam, J. H., Schrock, R. R. (1993), J. Am. Chem. Soc. 115, 11831.
113. Park, L. Y., Steiglitz, S. G., Crowe, W. M., Schrock, R. R. (1991), Macromolecules 24, 3489.
114. Percec, V. Pugh, C. (1989), in: Side Chain Liquid Crystal Polymers: McArdle, C. B. (Ed.). New York: Chapman and Hall, p. 30.
115. Perego, G., Lugli, G., Pedretti, U. (1985), Mol. Cryst. Liq. Cryst. 117, 59.
116. Poshyachinda, S., Edwards, H. G. M., Johnson, A. F. (1991), Polymer 32, 334.
117. Pugh, C., Schrock, R. R. (1992), Macromolecules 25, 6593.
118. Quignard, F., Leconte, M., Basset, J.-M. (1986), J. Mol. Catal. 36, 13.
119. Quignard, F., Leconte, M., Basset, J.-M., Hsu, L.-Y., Alexander, J. J., Shore, S. G. (1987), Inorg. Chem. 26, 4272.
120. Rempp, P., Merrill, E. W. (1986), Polymer Synthesis. New York: Huthig and Wepf.
121. Rinehart, R. E., Smith, H. P. (1965), Polym. Lett. 3, 1049.
122. Rizmi, M. (1997), Ph. D. Thesis, University of Durham, U. K.
123. Sailor, M. J., Ginsburg, E. J., Gorman, C. B., Kumar, A., Grubbs, R. H., Lewis, N. S. (1990), Science 249, 1146.
124. Sankaran, V., Cummins, C. C., Schrock, R. R., Cohen, R. E., Silby, R. J. (1990), J. Am. Chem. Soc. 112, 6858.
125. Sankaran, V., Cohen, R. E., Cummins, C. C., Schrock, R. R. (1991), Macromolecules 24, 6664.
126. Saunders, R. S., Cohen, R. E., Schrock, R. R. (1991), Macromolecules 24, 5599.
127. Schaverien, C. J., Dewan, J, C., Schrock, R. R. (1986), J. Am. Chem. Soc. 108, 2771.
128. Schlund, R., Schrock, R. R., Crowe, W. E. (1989), J., Am. Chem. Soc. 111, 8004.
129. Schrock, R. R. (1986), in: Reactions of Coordinated Ligands, Vol. 1: Braterman, P. S. (Ed.). New York: Plenum.
130. Schrock, R. R. (1990a), Acc. Chem. Res. 23, 158.
131. Schröck. R. R. (1990b), Acc. Chem. Res. 23, 158.
132. Schrock, R. R. (1993), in: Ring-Opening Polymerisation: Bruneile, D. J. (Ed.). Munich: Hanser, p. 129.
133. Schrock, R. R. (1994), Pure Appl. Chem. 66, 1447.
134. Schrock, R. R., Messerle, L. W., Wood, C. D., Guggenberger, L. J. (1978), J. Am. Chem. Soc. 100, 3793.
135. Schrock, R. R., Feldman, J., Grubbs, R. H., Cannizzo, L. (1987), Macromolecules 20, 1169.
136. Schrock, R. R., DePue, R. T., Feldman, J., Schaverien. C. J., Dewan, J. C., Liu, A. H. (1988a), J. Am. Chem. Soc. 110, 1423.
137. Schrock, R. R., Krouse, S. A., Knoll, K., Feldman, J., Murdzek. J. S., Yang, D. C. (1988b), J. Mol. Catal. 46, 243.
138. Schrock, R. R., Yap, K. B., Yang, D. C., Sitzmann, H., Sita, L. R., Bazan, G. C. (1989), Macromolecules 22, 3191.
139. Schrock, R. R., Murdzek, J. S., Bazan, G. C., Robbins, J., DiMare, M., O'Regan, M. (1990), J. Am. Chem. Soc. 112, 3875.
140. Schrock, R. R., Crowe, W. E., Bazan, G. C., DiMare, M., O'Regan, M: B., Schofield, M. H. (1991), Organometallics 10, 1832.
141. Schultz, W. J., Etter, M. C., Pocius, A. V., Smith, S. (1980), J. Am. Chem. Soc. 102, 7982.
142. Schuster, M. C., Mortell, K. H., Hegeman, A. D., Kiessling, L. L. (1997), J. Mol. Cat. A: Chem. 116, 209.
143. Schwab, P., Grubbs, R. H., Ziller, J. W. (1996), J. Am. Chem. Soc. 118, 100.
144. Shirakawa, H., Ikeda, S. (1971), Polym. J. 2, 231.
145. Shirakawa, H., Louis, E. J., MacDiarmid, A. G., Chiang, C. K., Heeger, A. J. (1977), J. Chem. Soc., Chem. Commun., 578.
146. Stille, J. R., Grubbs, R. H., (1986), J. Am. Chem. Soc. 108, 855.
147. Stille, J. R., Santarsiero, B. D., Grubbs, R. H. (1990), J. Org. Chem. 55, 843.
148. Swager, T. M., Grubbs, R. H. (1989), J. Am. Chem. Soc. 111, 4413.
149. Swager, T. M., Dougherty, D. A., Grubbs, R. H. (1988), J. Am. Chem. Soc. 110, 2973.
150. Tebbe, F. N., Parshall, G. W., Ovenall, D. W. (1979), J. Am. Chem. Soc 101, 5074.
151. Toreki, R., Schrock, R. R., Davis, W. M. (1992), J. Am. Chem. Soc. 114, 3367.
152. Winkler, B., Ungerank, M., Stelzer, F. (1996), Macromol. Chem. Phys. 197, 2343.
153. Wagener, K. B., Boncella, G. M., Nel, J. G. (1991), Macromolecules 24, 2649.
154. Webster, O. W. (1991), Science 251, 887.
155. Weck, M., Schwab, P., Grubbs, R. H. (1996), Macromolecules 29, 1789.
156. Weck, M., Mohr, B., Maughon, B. R., Grubbs, R. H. (1997), Macromolecules 30, 6430.
157. Whatmore, R. W. (1986), Rep. Progs. Phys. 49, 1335.
158. Wittbecker, E. L., Hall, H. K., Campbell, T. W. (1960), J. Am. Chem. Soc. 82, 1218.
159. Woodward, A. E. (1988), Atlas of Polymer Morphology. Munich: Hanser.
160. Wu, Z., Wheeler, D. R., Grubbs, R. H. (1992), J. Am. Chem. Soc. 114, 146.
161. Wu, Z., Benedicta, A. D., Grubbs, R. H. (1993), Macromolecules 26, 4975.
162. Yang, Z., He, Y., Vourloumis, D., Vallberg, H., Nicolaou, K. C. (1997), Angew. Chem. Int. Ed. Engl. 36, 166.