Syndioselective MMA polymerization by group 4 constrained geometry catalysts: A combined experimental and theoretical study

Macromolecules

Volumn 41, Issue 19, 2008, Pages 6910-6919

  Ning, Yalan ^a   Caporaso, Lucia ^b   Correa, Andrea ^b   Gustafson, Laura O ^a   Cavallo, Luigi ^b   Chen, Eugene Y X ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT TEMPERATURES; CATALYST CONCENTRATIONS; CATALYST SITES; COMPARATIVE STUDIES; CONSTRAINED GEOMETRIES; COUNTERION; DENSITY FUNCTIONAL CALCULATIONS; ENOLATE; EPIMERIZATION; GROUP 4; ISOPROPYL ESTERS; ISOSTRUCTURAL; MMA POLYMERIZATIONS; OPENING PROCESSES; ORDER KINETICS; POLYMERIZATION OF METHYL METHACRYLATES; SOLVENT POLARITIES;

ABS RESINS; CATALYSIS; CATALYSTS; CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY; ESTERS; MONOMERS; ORGANIC COMPOUNDS; POLYMERIZATION; POLYMERS; SILICON; STEREOSELECTIVITY; ZIRCONIUM;

ACRYLIC MONOMERS;

EID: 54949097817     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma801494g     Document Type: Article

References (122)

1. Selected reviews: (a) Chen, E. Y.-X.; Rodriguez-Delgado, A. In Comprehensive Organometallic Chemistry III; Bochmann, M., Vol. Ed.; Mingos, M. P., Crabtree, R. H., Chief Eds.; Elsevier: Oxford, 2007; Vol. 4, pp 759-1004.
2. (b) Cuenca, T. In Comprehensive Organometallic Chemistry III; Bochmann, M., Vol. Ed.; Mingos, M. P., Crabtree, R. H., Chief Eds.; Elsevier: Oxford, 2007; Vol. 4, pp 323-696.
3. (c) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255-270.
4. (d) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-387.
5. Selected books, book chapters, or special journal issues: (a) Stereo-selective Polymerisation with Single-Site Catalysts; Baugh, L. S., Canich, J. A. M., Eds.; CRC Press: Boca Raton, FL, 2008.
6. (b) Resconi, L.; Chadwick, J. C.; Cavallo, L. In Comprehensive Organometallic Chemistry III; Bochmann, M., Vol. Ed.; Mingos, M. P., Crabtree, R. H., Chief Eds.; Elsevier: Oxford, 2007; Vol. 4, pp 1005-1166.
7. (c) Marks, T. J., Ed. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15288-15354, and contributions therein (issue on "Polymerization Special Feature").
8. (d) Gladysz, J. A., Ed. Chem. Rev. 2000, 100, 1167-1681, and contributions therein (issue on Frontiers in Metal-Catalyzed Polymerization).
9. (e) Marks, T. J., Stevens, J. C., Eds. Top. Catal. 1999, 7, 1-208, and contributions therein (issue on Advances in Polymerization Catalysis. Catalysts and Processes).
10. (f) Metalorganic Catalysts for Synthesis and Polymerization: Recent Results by Ziegler-Natta and Metallocene Investigations; Kaminsky, W., Ed.; Springer-Verlag: Berlin, 1999.
11. (g) Jordan, R. F., Ed. J. Mol. Catal. A: Chem. 1998, 128, 1-337, and contributions therein (issue on Metallocene and Single-Site Olefin Catalysts)
12. (h) Metallocenes: Synthesis - Reactivity-Applications; Togni A., Halterman, R. L., Eds.; Wiley-VCH: Weinheim, 1998.
13. (i) Ziegler Catalysts; Mülhaupt, R., Brintzinger, H.-H., Eds.; Springer-Verlag: Berlin, 1995.
14. (j) Soga, K., Terano, M., Eds. Stud. Surf. Sci. Catal. 1994, 89, 1-410, and contributions therein (issue on Catalyst Design for Tailor-Made Polyolefins).
15. Selected reviews: (a) Chen, E. Y.-X. J. Polym. Sci., Pan A: Polym. Chem. 2004, 42, 3395-3403.
16. (b) Boffa, L. S.; Novak, B. M. Chem. Rev. 2000, 100, 1479-1493.
17. Ning, Y.; Chen, E. Y.-X. J. Am. Chem. Soc. 2008, 130, 2463-2465.
18. Mariott, W. R.; Escudé, N. C.; Chen, E. Y.-X. J. Polym. Scci., Part A: Polym. Chem. 2007, 45, 2581-2592.
19. Lian, B.; Thomas, C. M.; Navarro, C.; Carpentier, J.-F. Organometallics 2007, 26, 187-195.
20. Ning, Y.; Chen, E. Y.-X. Macromolecules 2006, 39, 7204-7215.
21. Rodriguez-Delgado, A.; Mariott, W. R.; Chen, E. Y.-X. J. Organomet. Chem. 2006, 697, 3490-3497.
22. Rodriguez-Delgado, A.; Chen, E. Y.-X. Macromolecules 2005, 38, 2587-2594.
23. Kostakis, K.; Mourmouris, S.; Kotakis, K.; Nikogeorgos, N.; Pitsikalis, M.; Hadjichristidis, N. J. Polym. Scci., Part A: Polym. Chem. 2005, 43, 3305-3314.
24. Ning, Y.; Cooney, M. J.; Chen, E. Y.-X. J. Organomet. Chem. 2005, 690, 6263-6270.
25. Lian, B.; Lehmann, C. W.; Navarro, C.; Carpentier, J.-F. Organometallics 2005, 24, 2466-2472.
26. Bolig, A. D.; Chen, E. Y.-X. J. Am. Chem. Soc. 2004, 126, 4897-4906.
27. Stojcevic, G.; Kim, H.; Taylor, N. J.; Marder, T. B.; Collins, S. Angew. Chem., Int. Ed. 2004, 43, 5523-5526.
28. Strauch, J. W.; Fauré, J.-L.; Bredeau, S.; Wang, C.; Kehr, G.; Fröhlich, R.; Luftmann, H.; Erker. G. J. Am. Chem. Soc. 2004, 126, 2089-2104.
29. Karanikolopoulos, G.; Batis, C.; Pitsikalis, M.; Hadjichristidis, N. J. Polym. Scci., Part A: Polym. Chem. 2004, 42, 3761-3774.
30. Ferenz, M.; Bandermann, F.; Sustmann, R.; Sicking, W. Macromol. Chem. Phys. 2004, 205, 1196-1205.
31. Rodriguez-Delgado, A.; Mariott, W. R.; Chen, E. Y.-X. Macromolecules 2004, 37, 3092-3100.
32. Lian, B.; Toupet, L.; Carpentier, J.-F. Chem.-Eur. J. 2004, 10, 4301-4307.
33. Jensen, T. R.; Yoon, S. C.; Dash, A. K.; Luo, L.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14482-14494.
34. Chen, E. Y.-X.; Cooney, M. J. J. Am. Chem. Soc. 2003, 125, 7150-7151.
35. Mariott, W. R.; Chen, E. Y.-X. J. Am. Chem. Soc. 2003, 125, 15726-15727.
36. Jin, J.; Mariott, W. R.; Chen, E. Y.-X. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3132-3142.
37. Batis, C.; Karanikolopoulos, G.; Pitsikalis, M.; Hadjichristidis, N. Macromolecules 2003, 36, 9763-9774.
38. Karanikolopoulos, G.; Batis, C.; Pitsikalis, M.; Hadjichristidis, N. Macromol. Chem. Phys. 2003, 204, 831-840.
39. Bolig, A. D.; Chen, E. Y.-X. J. Am. Chem. Soc. 2002, 124, 5612-5613.
40. Jin, J.; Chen, E. Y.-X. Organometallics 2002, 21, 13-15.
41. Jin, J.; Wilson, D. R.; Chen, E. Y.-X. Chem. Commun. 2002, 708, 709.
42. Jin, J.; Chen, E. Y.-X. Macromol. Chem. Phys. 2002, 203, 2329-2333.
43. Bandermann, F.; Ferenz, M.; Sustmann, R.; Sicking, W. Macromol. Symp. 2001, 174, 247-253.
44. Karanikolopoulos, G.; Batis, C.; Pitsikalis, M.; Hadjichristidis, N. Macromolecules 2001, 34, 4697-4705.
45. Bolig, A. D.; Chen, E. Y.-X. J. Am. Chem. Soc. 2001, 123, 7943-7944.
46. Frauenrath, H.; Keul, H.; Höcker, H. Macromolecules 2001, 34, 14-19.
47. Nguyen, H.; Jarvis, A. P.; Lesley, M. J. G.; Kelly, W. M.; Reddy, S. S.; Taylor, N. J.; Collins, S. Macromolecules 2000, 33, 1508-1510.
48. Bandermann, F.; Ferenz, M.; Sustmann, R.; Sicking, W. Macromol. Symp. 2000, 161, 127-134.
49. Cameron, P. A.; Gibson, V.; Graham, A. J. Macromolecules 2000, 33, 4329-4335.
50. Stuhldreier, T.; Keul, H.; Höcker, H. Macromol. Rapid Commun. 2000, 21, 1093-1098.
51. Chen, E. Y.-X.; Metz, M. V.; Li, L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 6287-6305.
52. Shiono, T.; Saito, T.; Saegusa, N.; Hagihara, H.; Ikeda, T.; Deng, H.; Soga, K. Macromol. Chem. Phys. 1998, 199, 1573-1579.
53. Hong, E.; Kim, Y.; Do, Y. Organometallics 1998, 17, 2933-2935.
54. Li, Y.; Ward, D. G.; Reddy, S. S.; Collins, S. Macromolecules 1997, 30, 1875-1883.
55. Deng, H.; Shiono, T.; Soga, K. Macromol. Chem. Phys. 1995, 196, 1971-1980.
56. Deng, H.; Shiono, T.; Soga, K. Macromolecules 1995, 28, 3067-3073.
57. Soga, K.; Deng, H.; Yano, T.; Shiono, T. Macromolecules 1994, 27, 7938-7940.
58. Collins, S.; Ward, D. G.; Suddaby, K. H. Macromolecules 1994, 27, 7222-7224.
59. Collins, S.; Ward, S. G. J. Am. Chem. Soc. 1992, 114, 5460-5462.
60. Lian, B.; Thomas, C. M.; Navarro, C.; Carpentier, J.-F. Macromolecules 2007, 40, 2293-2294.
61. Mariott, W. R.; Rodriguez-Delgado, A.; Chen, E. Y.-X. Macromolecules 2006, 39, 1318-1327.
62. Kostakis, K.; Mourmouris, S.; Pitsikalis, M.; Hadjichristidis, N. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 3337-3348.
63. Deng, H.; Soga, K. Macromolecules 1996, 29, 1847-1848.
64. Miyake, G. M.; Chen, E. Y.-X. Macromolecules 2008, 41, 3405-3416.
65. Miyake, G. M.; Mariott, W. R.; Chen, E. Y.-X. J. Am. Chem. Soc. 2007, 129, 6724-6725.
66. Mariott, W. R.; Chen, E. Y.-X. Macromolecules 2005, 38, 6822-6832.
67. Mariott, W. R.; Chen, E. Y.-X. Macromolecules 2004, 37, 4741-4743.
68. Spaether, W.; Klass, K.; Erker, G.; Zippel, F.; Fröhlich, R. Chem.-Eur. J. 1998, 4, 1411-1417.
69. Caporaso, L.; Cavallo, L. Macromolecules 2008, 41, 3439-3445.
70. Caporaso, L.; Gracia-Budrìa. J.; Cavallo, L. J. Am. Chem. Soc. 2006, 128, 16649-16654.
71. Tomasi, S.; Weiss, H.; Ziegler, T. Organometallics 2007, 26, 2157-2166.
72. Tomasi, S.; Weiss, H.; Ziegler, T. Organometallics 2006, 25, 3619-3630.
73. Hölscher, M.; Keul, H.; Höcker, H. Macromolecules 2002, 35, 8194-8202.
74. Hölscher, M.; Keul, H.; Höcker, H. Chem.-Eur. J. 2001, 7, 5419-5426.
75. Sustmann, R.; Sicking, W.; Bandermann, F.; Ferenz, M. Macromolecules 1999, 32, 4204-4213.
76. (a) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623-4640.
77. (b) Okuda, J. Comments Inorg. Chem. 1994, 16, 185-205.
78. (c) Okuda, J. Chem. Ber. 1990, 123, 1649-1651.
79. (d) Shapiro, P. J.; Bunel, E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867-869.
80. (e) Piers, W. E.; Shapiro, P. J.; Bunel, E.; Bercaw, J. E. Synlett 1990, 2, 74-84.
81. (a) Guo, N.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2008, 130, 2246-2261.
82. (b) Motta, A.; Fragalà, I. L.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7327-7338.
83. (c) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-315.
84. (d) Chum, P. S.; Kruper, W. J.; Guest, M. J. Adv. Mater. 2000, 12, 1759-1767.
85. (e) McKnight. A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598.
86. (f) Stevens, J. C. Stud. Surf. Sci. Catal. 1996, 101, 1120;
87. 1994, 89, 277-284.
88. (g) Canich, J. A. Eur. Pat. Appl. EP 0420436 A1, 1991.
89. (h) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Eur. Pat. Appl. EP 0 416815 A2, 1991.
90. Allen, R. D.; Long. T. E.; McGrath, J. E. Polym. Bull. 1986, 15, 127-134.
91. Feng, S.; Roof, G. R.; Chen, E. Y.-X. Organometallics 2002, 21, 832-839.
92. (a) Lee, C. H.; Lee, S. J.; Park, J. W.; Kim, K. H.; Lee, B. Y.; Oh, J. S. J. Mol. Catal., A: Chem. 1998, 132, 231-239.
93. (b) Biagini, P.; Lugli, G.; Abis, L.; Andreussi, P. U.S. Pat. 5,602269, 1997.
94. (a) Resconi, L.; Camurati, I.; Grandini, C.; Rinaldi, M.; Mascellani, N.; Traverso, O. J. Organomet. Chem. 2002, 664, 5-26.
95. (b) Carpentier, J.-F.; Maryin, V. P.; Luci, J.; Jordan, R. F. J. Am. Chem. Soc. 2001, 123, 898-909.
96. Chen, Y.-X.; Marks, T. J. Organometallics 1997, 16, 3649-3657.
97. Kim, Y.-J.; Bernstein, M. P.; Galiano Roth, A. S.; Romesberg, F. E.; Williard, P. G.; Fuller, D. J.; Harrison, A. T.; Collum, D. B. J. Org. Chem. 1991, 56, 4435-4439.
98. Rodriguez-Delgado, A.; Chen, E. Y.-X. J. Am. Chem. Soc. 2005, 127, 961-974.
99. (a) Brar, A. S.; Singh, G.; Shankar, R. J. Mol. Struct. 2004, 703, 69-81.
100. (b) Bovey, F. A.; Mirau, P. A. NMR of Polymers; Academic Press: San Diego, CA, 1996.
101. (c) Kawamura, T.; Toshima, N.; Matsuzaki, K. Makromol. Chem., Rapid Commun. 1993, 14, 719-724.
102. (d) Chujo, R.; Hatada, K.; Kitamaru, R.; Kitayama, T.; Sato, H.; Tanaka, Y. Polym. J. 1987, 19, 413-424.
103. (e) Ferguson, R. C.; Ovenall, D. W. Macromolecules 1987, 20, 1245-1248.
104. (f) Ferguson, R. C.; Ovenall, D. W. Polym. Prepr. 1985, 26, 182-183.
105. (g) Subramanian, R.; Allen, R. D.; McGrath, J. E.; Ward, T. C. Polym. Prepr. 1985, 26, 238-240.
106. (a) ADF2007 Theoretical Chemistry, Vrije Universiteit, Amsterdam, 2007, Users's Manual.
107. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41-51.
108. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
109. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
110. (a) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
111. (b) Perdew, J. P. Phys. Rev. B 1986, 34, 7406-7406.
112. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 1993, 799-805.
113. (b) Pye, C. C.; Ziegler, T. Theor. Chem. Acc. 1999, 101, 396-408.
114. Ahlrichs, R.; Bar, M.; Haser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, 165-169.
115. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3302.
116. (a) Haeusermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 78, 1211-1224.
117. (b) Kuechle, W.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1994, 100, 7535-7542.
118. (c) Leininger, T.; Nicklass, A.; Stoll, H.; Dolg, M.; Schwerdtfeger, P. J. Chem. Phys. 1996, 105, 1052-1059.
119. Chen, M.-C.; Roberts, J. A. S.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 4605-4625.
120. Ning, Y.; Zhu, H.; Chen, E. Y.-X. J. Organomet. Chem. 2007, 692, 4535-4544.
121. Lohrenz, J. C. W.; Woo, T. K.; Ziegler, T. J. Am. Chem. Soc. 1995, 117, 12793-12800.
122. Tomasi, S.; Razavi, A.; Ziegler, T. Organometallics 2007, 26, 2024-2036.