Palladium catalysts for norbornene polymerization. A study by NMR and calorimetric methods

Organometallics

Volumn 27, Issue 15, 2008, Pages 3761-3769

  Casares, Juan A ^a   Espinet, Pablo ^a   Salas, Gorka ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ABS RESINS; CHEMICAL REACTIONS; MONOMERS; NUCLEAR MAGNETIC RESONANCE; PALLADIUM; POLYMERS;

CALORIMETRIC METHODS; NORBORNENE POLYMERIZATION; PALLADIUM CATALYSTS;

CATALYSTS;

EID: 50549084667     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800264a     Document Type: Article

References (84)

1. (a) Janiak, C.; Lassahn, P. G. J. Mol. Catai. A: Chem. 2001, 166, 193-209.
2. (b) Janiak, C.; Lassahn, P. G. Macromol. Rapid Commun. 2001, 22, 479-492.
3. (a) Karafilidis, C.; Hermann, H.; Rufinska, A.; Gabor, B.; Mynott, R. J.; Breitenbruch, G.; Weidenthaler, C.; Rust, J.; Joppek, W.; Brookhart, M. S.; Thiel, W.; Fink, G. Angew. Chem., Int. Ed. 2004, 43, 2444-2446.
4. (b) Karafilidis, C.; Angermund, K.; Gabor, B.; Rufinska, A.; Mynott, R. J.; Breitenbruch, G.; Thiel, W.; Fink, G. Angew. Chem., Int. Ed. 2007, 46, 3745-3749.
5. (a) Peruch, F.; Cramail, H.; Deffieux, A. Macromol. Chem. Phys. 1998, 199, 2221-2227.
6. (b) Arndt, M.; Gosmann, M. Polym. Bull. 1998, 41, 433-440.
7. (c) Mast, C.; Krieger, M.; Dehnicke, K.; Greiner, A. Macromol. Rapid Commun. 1999, 20, 232-235.
8. (d) Zhao, C-T.; Ribeiro, M. R.; Portela, M. F. J. Mol. Catal. A Chem. 2002, 185, 81-85.
9. (e) Li, Y.-S.; Li, Y.-R.; Li, S.-F. J. Organomet. Chem. 2003, 667, 185-191.
10. (f) Zhang, D.; Jin, G.-X.; Weng, L.-H.; Wang, F. Organometallics 2004, 23, 3270-3275.
11. (g) Nelkenbaum, E.; Kapon, M.; Eisen, M. S. J. Organomet. Chem. 2005, 690, 3154-3164.
12. (a) Lassahn, P. G.; Janiak, C.; Oh, J.-S. Macromol. Rapid Commun. 2002, 23, 16-20.
13. (b) Janiak, C.; Lassahn, P. G. Polym. Bull. 2002, 47, 539-546.
14. (c) Lassahn, P. G.; Lozan, V.; Wu, B.; Weller, A. S.; Janiak, C. Dalton Trans. 2003, 4437-4450.
15. (d) Jang, Y.; Sung, H. K.; Lee, S.; Bae, C. Polymer 2005, 46, 11301-11310.
16. Goodall, B. L. In Late Transition Metal Polymerization Catalysis; Rieger, B., Saunders Baugh, L., Katcker, S., Striegler, S., Eds.;Wiley-VCH: Weinheim, Germany, 2003; Chapter 4.
17. (a) Sacchi, M. C.; Sonzogni, M.; Losio, S.; Forlini, F.; Locatelli, P.; Tritto, I.; Licchelli, M. Macromol. Chem. Phys. 2001, 202, 2052-2058.
18. (b) Zhao, C.; Ribeiro, R.; Subrahmayam, V. S.; Gil, C. L.; de Lima, A. P. Polymer 2001, 42, 2455-2462.
19. (c) Janiak, C.; Lasshahn, P.-G. Polym. Bull. 2002, 47, 539-546.
20. Diamanti, S. J.; Ghosh, P.; Shimizu, F.; Bazan, G. C. Macromolecules 2003, 36, 9731-9735.
21. Lee, B. Y.; Kim, Y. H.; Shin, H. J.; Lee, C. H. Organometallics 2002, 21, 3481-3484.
22. Sun, W.-H.; Yang, H.; Li, Z.; Li, Y. Organometallics 2003, 22, 3678-3683.
23. Benedikt, G. M.; Elce, E.; Goodall, B. L.; Kalamarides, H. A.; McIntosh, L. H., Ill; Rhodes, L. F.; Selvy, K. T.; Andes, C.; Oyler, K.; Sen, A. Macromolecules 2002, 35, 8978-8988.
24. Barnes, D. A.; Benedikt, G. M.; Goodall, B. L.; Huang, S. S.; Kalamarides, H. A.; Lenhard, S.; McIntosh, L. H. III.; Selvy, K. T.; Shick, R. A.; Rhodes, L. F. Macromolecules 2003, 36, 2623-2632.
25. Huang, C.-F.; Wang, S.-K.; Kuo, S.-W.; Huang, W.-J.; Chang, F.C. J. Appl. Polym. Sci. 2004, 92, 1824-1833.
26. For the polymerization of functionalized norbornenes, see: (a) Breunig, S.; Risse, W. Makromol. Chem. 1992, 193, 2915-2927.
27. (b) Reinmuth, A.; Mathew, J. P.; Melia, J.; Risse, W. Macromol. Rapid Commun. 1996, 17, 173-180.
28. (c) Mathew, J. P.; Reinmuth, A.; Melia, J.; Swords, N.; Risse, W. Macromolecules 1996, 29, 2755-2763.
29. (d) Heinz, B. S.; Alt, F. P.; Heitz, W. Macromol. Rapid Commun. 1998, 19, 251-256.
30. (e) Shin, B.; Jang, M.; Yoon, D. Y.; Heitz, W. Macromol. Rapid Commun. 2004, 25, 728-732.
31. Yamashita, M.; Takamiya, I.; Jin, K.; Nozaki, K. Organometallics 2006, 25, 4588-4595.
32. Lipian, J.; Mimna, R. A.; Fondran, J. C.; Yandulov, D.; Shick, R. A.; Goodall, B. L.; Rhodes, L. F.; Huffman, J. C. Macromolecules 2002, 35, 8969-8977.
33. Kang, M.; Sen, A. Organometallics 2004, 23, 5396-5398.
34. (a) Hennis, A. D.; Polley, J. D.; Long, G. S.; Sen, A.; Yandulov, D.; Lipian, J.; Benedikt, G. M.; Rhodes, L. F. Organometallics 2001, 20, 2802-2812.
35. (b) Funk, J. K.; Andes, C. E.; Sen, A. Organometallics 2004, 23, 1680-1683.
36. (a) Sen, A.; Lai, T. W. Organometallics 1982, 1, 415-417.
37. (b) Sen, A.; Lai, T. W.; Thomas, R. R. J. Organomet. Chem. 1988, 358, 567-568.
38. (c) Goodall, B. L.; Jayaraman, S.; Shick, R. A.; Rhodes, L. F.; Allen, R. D.; DiPietro, R. A.; Wallow, T. U.S. Patent 6,723,486, 2004.
39. (d) Chemtob, A.; Gilbert, R. G. Macromolecules 2005, 38, 6796-6805.
40. (e) Myagmarsuren, G.; Jeong, O. Y.; Ihm, S. K. Appl. Catai., A 2005, 296, 21-29.
41. (f) Myagmarsuren, G.; Lee, K. S.; Jeong, O. Y.; Ihm, S. K. Catal. Commun. 2005, 6, 337-342.
42. (g) Myagmarsuren, G.; Lee, K. S.; Jeong, O. Y.; Ihm, S. K. Polymer 2005, 46, 3685-3692.
43. Casares, J. A.; Espinet, P.; Martin-Alvarez, J. M.; Martinez-Ilarduya, J. M.; Salas, G. Eur. J. Inorg. Chem. 2005, 3825-3831.
44. Casares, J. A.; Espinet, P.; Martinez-Ilarduya, J. M.; Mucientes, J. J.; Salas, G. Inorg. Chem. 2007, 46 (3);), 1027-1032.
45. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
46. (a) Mingos, D. M. P.; Müller, T. E. J. Organomet. Chem. 1995, 500, 251-259.
47. (b) Müller, T. E.; Mingos, D. M. P. Transition Met. Chem. 1995, 20, 533-539.
48. 4. The formation of polynorbornene as a white precipitate started immediately. The solution was stirred for 24 h, and the solid was filtered and washed with EtOH.
49. 5 groups are very different and are clearly identified; see for instance: (a) Albéniz, A. C.; Espinet, P.; Foces-Foces, C.; Cano, F. H. Organometallics 1990, 9, 1079-1085.
50. (b) Albéniz, A. C.; Espinet, P.; Jeannin, Y.; Philoche-Levisalles, M.; Mann, B. E. J. Am. Chem. Soc. 1990, 112, 6594-6600.
51. (c) Albéniz, A. C.; Espinet, P. Organometallics 1991, 10, 2987-2988.
52. Formation of soluble low-molecular-weight oligomers can explain why no polymer is observed to precipitate in methanol in attempts at polymerization with neutral complexes as catalysts.
53. Sen, A. Acc Chem. Res. 1988, , 421-428.
54. One of the bands is assigned to v(CN) stretching and the other to a combination band: Storhoff, B. N.; Lewis, H. C Coord. Chem. Rev. 1977, 23, 1-29.
55. The high concentration of palladium complex required to record a IR spectrum precluded the use of an excess of norbornene comparable to the ratio used in the catalytic experiments.
56. For the use of calorimetry on catalysis kinetics see for instance: (a) LeBlond, C.; Wang, J.; Larsen, R. D.; Orella, C. J.; Forman, A. L.; Landau, R. N.; Laquidara, J., Jr.; Blackmond, D. G.; Sun, Y.-K. Thermochim. Acta 1996, 289, 189-207.
57. (b) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104-14114.
58. (c) Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362.
59. (d) Zogg, A.; Stoessel, F.; Fischer, U.; Hungerbühler, K. Thermochim. Acta 2004, 419, 1-17.
60. (e) Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320.
61. For the use of calorimetry on kinetics of polymerization reactions see: (a) Bechthold, N.; Landfester, K. Macromolecules 2000, 33, 4682-4689.
62. (b) Karlsson, O. J.; Hassander, H.; Wesslén, B. J. Appl. Polym. Sci. 2000, 77, 297-311.
63. (c) Saethre, B. Polym. Int. 1998, 45, 222-228.
64. For a discussion of the relationship between heat flow and reaction rates see refs 34d,e and the Supporting Information of ref 34c.
65. Cross, R. J. Adv. Inorg. Chem. 1989, 34, 219-291.
66. For associative and dissociative substitution processes in sterically hindered complexes see (a) Bartolomé, C.; Espinet, P.; Martin-Alvarez, J. M.; Villafafle, F. Eur. J. Inorg. Chem. 2003, 3127-3138.
67. (b) Bartolomé, C.; Espinet, P.; Martin-Alvarez, J. M.; Villafañe, F. Eur. J. Inorg. Chem. 2004, 2326-2337.
68. The NB consumed before the second injection is known from the integrated area of the curve.
69. 3 is necessary: Casado, A. L.; Espinet, P. Organometallics 2003, 22, 1305-1309.
70. See also (a) Albéniz, A. C.; Casado, A. L.; Espinet, P. Inorg. Chem. 1999, 38, 2510-2515.
71. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959.
72. 19
73. Funk, J. K.; Andes, C. E.; Sen, A. Organometallics 2004, 23, 1680-1683.
74. (a) Sen, A. Acc. Chem. Res. 1993, 26, 303-310.
75. (b) Markies, B.; Kruis, D.; Rietveld, M. H. P.; Verkerk, K. A. N.; Boersma, J.; Kooijman, H.; Lakin, M. T.; Speck, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 5263-5274.
76. (c) Delis, J. G. P.; Aubel, P. B.; Vrieze, D.; van Leeuwen, P. W. N. M.; Veldman, N.; Spek, A. L. Organometallics 1997, 16, 4150-4160.
77. Integration of IR signals gives only a rough estimation of the composition. It was used because NMR integration should be based on integration the aliphatic signals versus the aldehydic proton. The latter gives an extremely broad signal. This, along with the large difference in intensity, makes compared integration impossible.
78. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, U.K., 1988.
79. Usón, R.; Fomiés, J.; Martínez, F.; Tomás, M. J. Chem. Soc., Dalton Trans. 1980, 888-893.
80. Usón, R.; Formés, J.; Nalda, J. A.; Lozano, M. J.; Espinet, P.; Albéniz, A. C Inorg. Chim. Acta 1989, 156, 251-256.
81. Bayse, C. A.; Luck, R. L.; Schelter, E. J. Inorg. Chem. 2001, 40, 3463-3467.
82. Espinet, P.; Martinez-Ilarduya, J. M.; Pérez-Briso, C.; Casado, A. L.; Alonso, M. A. J. Organomet. Chem. 1998, 551, 9-20.
83. +.
84. Dilution heat of complexes was found to be negligible in our case.