Synthesis of palladium(II) pyridyl acylhydrazone complexes and application to homo- and copolymerization of cyclic olefins

Inorganic Chemistry Communications

Volumn 11, Issue 2, 2008, Pages 215-219

  Ogata, Kenichi ^a   Watanabe, Atsuo ^a   Yunokuchi, Tomoshige ^a   Toyota, Akinori ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Cyclic olefin; Norbornene; Palladium complex; Polymerization; Tetracyclododecene

Indexed keywords

EID: 38549165299     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2007.11.024     Document Type: Article

References (47)

1. Johnson L.K., Killian C.M., and Brookhart M. J. Am. Chem. Soc. 117 (1995) 6414
2. Killian C.M., Tempel D.J., Johnson L.K., and Brookhart M. J. Am. Chem. Soc. 118 (1996) 11664
3. Jonson L.K., Mecking S., and Brookhart M. J. Am. Chem. Soc. 118 (1996) 267
4. Killian C.M., Johnson L.K., and Brookhart M. Organometallics 16 (1997) 2005
5. Mecking S., Johnson L.K., Wang L., and Brookhart M. J. Am. Chem. Soc. 120 (1998) 888
6. Svejda S.A., Johnson L.K., and Brookhart M. J. Am. Chem. Soc. 121 (1999) 10634
7. Gates D.P., Svejda S.A., Onate E., Killian C.M., Johnson L.K., White P.S., and Brookhart M. Macromolecules 33 (2000) 2320
8. Guan Z., Cotts P.M., McCord E.F., and Mclain S. Science 283 (1999) 2059
9. Done M.C., Rüther T., Cavell K.J., Kilner M., Peacock E.J., Braussaud N., Skelton B.W., and White A. J. Organomet. Chem. 607 (2000) 78
10. Abu-Surrah A.S., Kettunen M., Lappalainen K., Piironen U., Klinga M., and Leskelä M. Polyhedron 21 (2002) 27
11. Laine T.V., Piironen U., Lappalainen K., Klinga M., Aitola E., and Leskelä M. J. Organomet. Chem. 606 (2000) 112
12. Chen R., and Mapolie S.F. J. Mol. Catal. A: Chem. 193 (2003) 33
13. Chen R., Bacsa J., and Mapolie S.F. Polyhedron 22 (2003) 2855
14. Mi X., Ma Z., Wang L., Ke Y., and Hu Y. Macromol. Chem. Phys. 204 (2003) 868
15. Zhang W., Sun W.-H., Wu B., Zhang S., Ma H., Li Y., Chen J., and Hao P. J. Organomet. Chem. 691 (2006) 4759
16. Groen J.H., Elsevier C.J., and Vrieze K. Organometallics 15 (1996) 3445
17. Groen J.H., Delis G.J.P., van Leeuwen P.W.N.M., and Vrieze K. Organometallics 16 (1997) 68
18. Delis J.G.P., Aubel P.G., Vrieze K., van Leeuwen P.W.N.M., Veldman N., Spek A.L., and van Neer F.J.R. Organometallics 16 (1997) 2948
19. Delis J.G.P., Aubel P.G., Vrieze K., and van Leeuwen P.W.N.M. Organometallics 16 (1997) 4150
20. Shareina T., Hillebrand G., Fuhrmann H., and Kempe R. Eur. J. Inorg. Chem. (2001) 2421
21. Shin D.M., Son S.U., Hong B.K., Chung Y.K., and Chun S.-H. J. Mol. Cat. A 210 (2004) 35
22. Benedikt G.M., Goodall B.L., Marchant N.S., and Rhodes L.F. New. J. Chem. 18 (1994) 105
23. Goodall B.L., Kroenke W., Minchak R.J., and Rhodes L.F. J. Appl. Polym. Sci. 47 (1992) 607
24. Haselwander T.F.A., Heitz W., Krugel S.A., and Wendorff J.H. Macromol. Chem. Phys. 197 (1996) 3435
25. Christ T., Greinewer A., Sander R., Stümpflen V., and Wendorff J.H. Adv. Mater. 9 (1997) 219
26. Naga N., and Imanishi Y. Macromol. Chem. Phys. 203 (2002) 159
27. Fujita M., and Coates G.W. Macromolecules 35 (2002) 9649
28. Simanke A.G., Mauler R.S., and Galland G.B. J. Polym. Sci. Part A: Polym. Chem. 40 (2002) 471
29. Wang W., Fuiki M., and Nomura K. J. Am. Chem. Soc. 127 (2005) 4582
30. Naga N. J. Polym. Sci. Part A: Polym. Chem. 43 (2005) 1285
31. Li X., and Hou Z. Macromolecules 38 (2005) 6767
32. Peruch F., Gtamail H., and Deffieux A. Macromol. Chem. Phys. 199 (1998) 2221
33. Zhao C.T., Ribeiro M.R., Portela M.F., Pereira S., and Nues T. Eur. Polym. J. 37 (2001) 45
34. Mi X., Ma Z., Wang L., Ke Y., and Hu Y. Macromol. Chem. Phys. 204 (2003) 868
35. Suzuki H., Matsumura S., Satoh Y., Sogoh K., and Yasuda H. React. Funct. Polym. 58 (2004) 77
36. Bao F., Lü X., and Chen Y. Polym. Bull. 58 (2007) 495
37. Kaminsky W., Beulich I., and Rosenau M.A. Macromol. Synp. 173 (2001) 211
38. Sagane T., Mizuno A., and Takata T. Makromol. Chem. 193 (1992) 2697
39. Hou J., Sun W.-H., Zhang D., Chen L., Li W., Zhao D., and Song H. J. Mol. Cat. A. 231 (2005) 221
40. K. Ogata, N. Nishimura, T. Yunokuchi, A. Toyota, Polymer J. Appl. Polym. Sci. accepted for publication.
41. For example. Hennis A.D., Polley J.G., Long G.S., Sen A., Yandulov D., Lipian J., Benedikt G.M., Rhodes L.F., and Huffman J.C. Organometallics 20 (2001) 2802
42. Lipian J., Mimna A.R., Fondran J.C., Yandulov D., Shick R.A., Goodall B.L., and Rhodes L.F. Macromolecules 35 (2002) 8969
43. Myagmarsuren G., Lee K., Jeong O., and Ihm S. Polymer 45 (2004) 3227
44. 3O: C, 72.57; H, 6.81; N, 14.94. Found: C, 72.60; H, 6.86; N, 15.02.
45. tBu), 7.4-9.5 (m, 9H, N{double bond, long}CH, Ph and Py), 12.1 (s, 1H, NH).
46. W = 0.1290. All data were collected on a RIGAKU RAXIS-RAPID diffractometer using MoKα radiation (0.71073 Å) at -173 °C. The structure was solved by the direct method and expanded using Fourier techniques. All non-hydrogen atoms were refined anisotropically and all hydrogen atoms were refined using riding model. The calculations were performed using the CrystalStructure crystallographic software package expect for refinement, which was performed using SHELXL-97. Atomic coordinates, thermal parameters, and bond distances and angles have been deposited at the Cambridge Crystallographic Data Center.
47. Polymerization procedure: Cycloolefin were placed in a 50 mL of flask containing a magnetic stirrer bar, and then solvent and MAO were added. To the cycloolefin and MAO solution, toluene solution of palladium complex was added at room temperature. After a desired time, the polymerization was quenched with acidified methanol. The precipitated polymer was filtered off, and washed with methanol, and then dried under vacuum for several hours at 60 °C. In case of cyclic olefin copolymerization, the copolymer was extracted with boiling o-dichlorobenzene.