Bis(imidodithiodiphosphinato) titanium and zirconium complexes: Synthesis, characterization, and their catalytic activity in the polymerization of α-Olefins

Organometallics

Volumn 28, Issue 8, 2009, Pages 2391-2400

  Chen, Fapu ^a   Kapon, Moshe ^a   Woollins D , ^b   Eisen, Moris S ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; ATACTIC POLYPROPYLENE; CATALYTIC ACTIVITY; GROUP 4; HIGH MOLECULAR WEIGHT; HOMOLEPTIC COMPLEX; IMIDO COMPLEXES; LOW TEMPERATURES; METAL OXIDATION; METHYLALUMOXANE; ZIRCONIUM COMPLEXES;

CATALYST ACTIVITY; CHELATION; COMPLEXATION; ELECTROCHEMICAL SENSORS; ETHYLENE; POLYDISPERSITY; POLYMERIZATION; POLYMERS; PROPYLENE; THERMOPLASTICS; TITANIUM; ZIRCONIUM; ZIRCONIUM COMPOUNDS;

TITANIUM COMPOUNDS;

EID: 65649116905     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om801176a     Document Type: Article

References (87)

1. For recent reviews of single-site olefin polymerization, see: (a) Li, H.; Marks, T. J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15295, and references therein.
2. Severn, J. R.; Chadwick, J. C.; Duchateau, R.; Friederichs, N. Chem. Rev. 2005, 105, 4073, and references therein.
3. Kaminsky, W. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3911.
4. Gladysz, J. A. Chem. Rev. 2000, 100 (special issue on Frontiers in Metal- Catalyzed Polymerization), and references therein.
5. Nayak, P. L. Popular Plastics Packaging 2003, 48, 86.
6. (a)Guo, N.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2008, 130, 2246, and references therein.
7. (b)Motta, A.; Fragala, I. L.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7327, and references therein.
8. (c)Naga, N. J Polym. Sci., Part A: Polym. Chem. 2005, 43, 1285.
9. Li H.;Li, L~ Schwartz, D. J.; Metz, M. V.; Marks, T. J.; Liable-Sands, L.; Rheingold, A. L. J. Am. Chem. Soc. 2005, 127, 14756, and references therein.
10. (e)Li H.;Stern C.L.; Marks, T. J. Macromolecules2005, 38, 9015, and references therein.
11. (f)Lee, S.-G.; Hong, S.-D.; Park, Y.-W.; Jeong, B.-G.; Nam, D.- W.; Jung, H. Y.; Lee, H.; Song, K. H. J. Organomet. Chem. 2004, 689, 2586.
12. (g)Kim I.; Ha, C.-S. Polym. Bull. 2004, 52, 133.
13. (h)Nomura K.;Fujita K.; Fujiki, M. J. Mol. Catal. A: Chem. 2004, 220, 133.
14. (i)Iedema, P. D.; Hoefsloot, H. C. J. Macromolecules 2003, 36, 6632.
15. (j)Klosin J.;Kruper, W. J., Jr.; Nickias, P. N.; Roof, G. R.; De Waele, P.; Abboud, K. A. Organometallics 2001, 20, 2663.
16. (k)McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587.
17. (a)Tritto I.;Boggioni L.; Ferro, D. R. Coord. Chem. Rev. 2006, 250, 212, and references therein.
18. (b)Hotta A.;Cochran E.;Ruokolainen J.;Khanna V.;Fredrickson G.H.;Kramer E.J.;Shin, Y.-W.; Shimizu,F.; Cherian, A. E.; Hustad, P. D.; Rose, J. M.; Coates, G. W. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15327, and references therein.
19. (c)Kaminsky W.;Tran, P.-D.; Werner, R. Macromol. Symp. 2004, 213, 101.
20. (d)Kim, E.-G.; Klein, M. L. Organometallics 2004, 23, 3319.
21. (e)Lavoie, A. R.; Ho, M. H.; Waymouth, R. M. Chem. Commun. 2003, 7, 864.
22. (f)Coates, G. W. Chem. Rev. 2000, 100, 1223.
23. (g)Ewen, J. A.; Jones, R. L.; Elder, M. J.; Camurati, I.; Pritzkow, H. Macromol. Chem. Phys. 2004, 205, 302.
24. (h)De Rosa, C.; Auriemma, F.; Circelli, T.; Longo, P.; Boccia, A. C. Macromolecules 2003, 36, 3465.
25. (a)Resconi L.; Cavallo L.; Fait L.; Fait A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253, and references therein.
26. (b)Rodriguez-Delgado, A.; Hannant, M. D.; Lancaster, S. J.; Bochmann, M. Macromol. Chem. Phys. 2004, 205, 334, and references therein.
27. (a)Volkis V.;Lisovskii A.; Eisen, M S. Stud. Surf. Sci. Catal. 2006, 161, 105, and references therein.
28. (b)Aharonovich S.;Volkis V.; Eisen, M. S. Macromol. Symp. 2007, 260, 165.
29. (c)Smolensky E.; Eisen, M. S. Dalton Trans. 2007, 5623, and references therein.
30. (d)Volkis V.;Averbuj C.; Eisen, M. S. J. Organomet. Chem. 2007, 692, 1940, references therein.
31. (e)Bambirra S.;Otten E.;van Leusen, D.; Meetsma, A.; Hessen, B. Zeit. Anorg. Allg. Chem. 2006, 632, 1950.
32. (f)Volkis V.;Rodensky M.;Lisovskii A.;Balazs Y.; Eisen, M. S. Organometallics 2006, 25, 4934.
33. (g)Lisovskii A.;Eisen, M. S. In Living and Controlled Polymerization: Synthesis, Characterization and Properties of the Respective Polymers and Copoly- mers; Jagur-GrodzinskiJ., Ed.; Nova Science Publishers, Inc., 2006; Chapter 10, p 343.
34. (h)Volkis V.;Lisovskii A.;Tumanskii B.;Shuster M.; Eisen, M. S. Organometallics 2006, 25, 2656.
35. (i)Volkis V.;Nelkenbaum E.;Lisovskii A.;Hasson G.;Semiat S.;Kapon M.;Botoshansky M.;Eishen Y.; Eisen, M. S. J. Am. Chem. Soc. 2003, 125, 2179.
36. (j)Volkis V.;Schmulinson M.;Shaviv E.;Lisovskii A.;Plat D.;Kuhl O.;Koch T.;Hey-Hawkins, E.; Eisen, M. S. In Beyond Metallocenes; Next Generation Polymerization Catalysts; Patiland, A. O., Hlatky,G. G., Eds.; American Chemical Society Symposium Series 857; 2003; p 46.
37. Smolensky E.;Kapon M.;Woollins J.D.; Eisen, M. S. Organo- metallics 2005, 24, 3255.
38. (a)Richter J.;Edelmann F.T.;Noltemeyer M.;Schmidt H.G.;Shmulinson M.; Eisen, M. S. J. Mol. Catal. Part A: Chem. 1998, 130, 149.
39. (b)Herskovics-Korine, D.; Eisen, M. S. J. Organomet. Chem. 1995, 503, 307.
40. (c)Lee, C. H.; La, Y.-H.; Park, J. W. Organometallics 2000, 19, 344.
41. (d)Mack H.; Eisen, M. S. J. Organomet. Chem. 1996, 525, 81.
42. (e)Mack H.; Eisen, M. S. J. Chem. Soc., Dalton Trans. 1998, 917.
43. (f)Averbuj C.;Tith E.; Eisen, M. S. J. Am. Chem. Soc. 1998, 120, 8640.
44. (g)Michael M.;Roesky H.W.;Stalke D.;Pauer F.;Henkel T.; Sheldrick, G. M. J. Chem. Soc., Dalton Trans. 1989, 2173.
45. Kuhl O.;Koch T.;Somoza F.B.;Junk P.C.;Hey-Hawkins, E.; Plat, D.; Eisen, M. S. J. Organomet. Chem. 2000, 604, 116.
46. Shmulinson M.;Galan-Fereres, M.; Lisovskii, A.; Nelkenbaum, E.; Semiat, Rafi.; Eisen, M. S. Organometallics 2000, 19, 1208.
47. (a)Jin X.; Novak, B. M. Macromolecules 2000, 33, 6205.
48. (b)Kim J.;Hwang, J.-W.; Kim, Y.; Lee, M. H.; Han, Y.; Do, Y. J. Organomet. Chem. 2001, 620,1.
49. Shaviv E.;Botoshanski M.; Eisen, M. S. J. Organomet. Chem. 2003, 683, 165-180.
50. (a)Schmidbaur H.;Lauteschlager S.; Kohler, F. H. J. Organomet. Chem. 1984, 271, 173.
51. (b)Schmidpeter A.; Groeger, H. Z. Anorg. Allgem. Chem. 1966, 345, 106.
52. X-ray structure of the free ligand has been reported, and the dimensional comparisons were made to the reference aquiring the best R factors. (a) Noth, H. Z. Naturforsch., Teil B 1982, 37, 1491.
53. (b)Husebye S.; Maartmann-Moe, K. Acta Chem. Scand, Ser. A 1983, 37, 439.
54. (c)Nixon, J. F.; Hitchcock, P. B. Inorg. Chim. Acta 1985, 96, 77.
55. Slawin, A. M. Z.; Ward, J.; Williams, D. J.; Woollins, J. D. J. Chem. Soc., Chem. Commum. 1994, 421.
56. Bailar, J. C. J. Inorg. Nucl. Chem. 1958, 8, 165.
57. Long, R. J.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2006, 45, 511.
58. Diethylamido complexes of Zr and Ti do not show normal methylene equivalence, and when observed, they are exhibited only at high temperatures. See for example ref 6.
59. Blake, A. J.; Collier, P. E.; Dunn, S. C.; Li, W.-S.; Mountford, P.; Shishkin, O. V. J. Chem. Soc., Dalton Trans. 1997, 1549.
60. Dunn, S. C.; Batsanov, A. S.; Mountford, P. J. Chem. Soc., Chem. Commun. 1994, 2007.
61. For late transition complexes, the boat/chair conformation has been observed; see: (a) Phillips, J. R.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J.; Woollins, J. D. J. Chem. Soc., Dalton Trans. 1995, 2467.
62. (b)Bhattacharyya P.;Slawin, A. M. Z.; Woollins, J. D. Polyhedron 2001, 20, 1831.
63. Straub T.;Haskel A.;Neyroud T.G.;Kapon M.;Botoshansky M.; Eisen, M. S. Organometallics 2001, 20, 5017.
64. (a)White, G. S.; Stephan, D. W. Inorg. Chem. 1985, 24, 1499.
65. (b)White, G. S.; Stephan, D. W. Organometallics 1987, 6, 2169.
66. (c)White, G. S.; Stephan, D. W. Organometallics 1988, 7, 903.
67. Matsuzaki K.;Kawaguchi H.;Voth P.;Noda K.;Itoh S.;Takagi H.D.;Kashiwabara K.; Tatsumi, K. Inorg. Chem. 2003, 42, 5320-5329.
68. Shannon, R. D. Acta Crystallogr. 1976, A32, 751-767.
69. Ray B.;Nuyrun T.G.;Kapon M.;Eichen Y.; Eisen, M. S. Organometallics 2001, 20, 3044.
70. Haskel A.;Wang J.Q.;Straub T.;Gueta-Neyroud, T.; Eisen, M. S. J. Am. Chem. Soc. 1999, 121, 3025.
71. Volkis V.;Nelkenbaum E.;Lisovskii A.;Hasson G.;Semiat, Rafi.; Kapon, M.; Botoshansky, M.; Eishen, Y.; Eisen, M. S. J. Am. Chem. Soc. 2003, 125, 2179.
72. (a)Smolensky E.;Kapon K.;Woollins D.J.; Eisen, M. S. Organometallics 2005, 24, 3255.
73. (b)Gueta-Neyroud, T.; Tumanskii, B.; Botoshansky, M.; Eisen, M. S. J. Organomet. Chem. 2007, 692, 927.
74. (c)Gornshtein F.;Kapon M.;Botoshansky M.; Eisen, M. S. Organometallics 2007, 26, 497.
75. Volkis V.;Tumanskii B.; Eisen, M. S. Organometallics 2006, 25, 2722.
76. See Supporting Information.
77. (a)Resconi L.;Cavallo L.;Fait A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253.
78. (b)Resconi L.;Piemontesi F.;Franciscono G.;Abis L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025.
79. Woolins, J. D. Inorganic Experiments; VCH: Weinheim, 1994; p145.
80. Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1960, 3857.
81. Diamond, G. M.; Jordan, R. F. Organometallics 1996, 15, 4030.
82. Ghesner I.;Palotas C.;Silvestru A.;Silvestru C.; Drake, J. E. Polyhedron 2001, 20, 1101.
83. Nonius. Kappa CCD Server Software; Nonius BV: Delft, The Netherlands, 1997.
84. Otwinowski Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
85. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
86. Sheldrick, G. M. SHELXL97. Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997.
87. Molecular Structure Corporation. ORTEP. TEXRAY Structure Analysis Package; MSC: The Woodlands, TX, 1999.