DOI QR코드

DOI QR Code

Novel Nickel Catalysts Containing Tetradentate Chelating Ligands for the Polymerization of Norbornene

  • Lee, Dong Hwan (Department of Chemistry, Inha University) ;
  • Lee, Jun Yong (Department of Fine Chemistry, Seoul National University of Technology) ;
  • Ryu, Ji Young (Department of Fine Chemistry, Seoul National University of Technology) ;
  • Kim, Youngmee (Division of Nano Sciences, Ewha Womans University) ;
  • Kim, Cheal (Department of Fine Chemistry, Seoul National University of Technology) ;
  • Lee, Ik-Mo (Department of Chemistry, Inha University)
  • Published : 2006.01.20

Abstract

New nickel complexes containing novel tetradentate ligands, 4,5-substituted-1,2-bis(pyridine-2-carboxamide)-benzene ligands but lacking alkyl or halide ligands in the coordination sphere have been prepared. They were activated with MMAO (modified methylaluminoxane) to be proven as efficient catalysts for the polymerization of norbornene. Both electron-donating and -withdrawing substituents on the benzene ring and polar solvents enhance the catalytic activity for olefin polymerization. Improvement in thermal stability of the complexes was observed. Some of these complexes were crystallographically determined to have square planar geometry. A plausible mechanism involving dissociation of ligands is proposed.

Keywords

References

  1. 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 and references therein https://doi.org/10.1021/om010232m
  2. Yang, H.; Li, Z.; Sun, W. H. J. Mol. Catal. A: Chemical 2003, 206, 23 and references therein https://doi.org/10.1016/S1381-1169(03)00426-6
  3. Janiak, C.; Lassahn, P. G. Macromol. Rapid Commun. 2001, 22, 479 https://doi.org/10.1002/1521-3927(20010401)22:7<479::AID-MARC479>3.0.CO;2-C
  4. Janiak, C.; Lassahn, P. G. J. Mol. Catal. A: Chemical 2001, 166, 193 https://doi.org/10.1016/S1381-1169(00)00475-1
  5. Sun, W. H.; Yang, J.; Li, Z.; Li, Y. Organometallics 2003, 22, 3678 and references therein https://doi.org/10.1021/om030018t
  6. Qing, W.; Yingying, I. J. Polym. Sci., Part A 2002, 42, 1421
  7. Hasan, T.; Ikeda, T.; Shiono, T. Macromolecules 2004, 37, 7432 https://doi.org/10.1021/ma049455p
  8. Hasan, T.; Nishii, K.; Shiono, T.; Ikeda, T. Macromolecules 2002, 35, 8933 https://doi.org/10.1021/ma025586j
  9. Kaminsky, W.; Bark, A.; Steiger, R. J. Mol. Catal. A: Chemical 1992, 109, 74
  10. Haselwander, T. F. A.; Heitz, W.; Krugel, S. A.; Wendorff, J. H. Macromol. Chem. Phys. 1996, 197, 3435 https://doi.org/10.1002/macp.1996.021971029
  11. Haselwander, T. F. A.; Heitz, W.; Krugel, S. A.; Wendorff, J. H. Macromolecules 1997, 30, 5345 https://doi.org/10.1021/ma970306z
  12. Benedikt, G. M.; Elce, E.; Goodall, B. L.; Kalamarides, H. A.; McIntosh, III, L. H.; Rhodes, L. F.; Selvy, K. T.; Andes, C.; Oyler, K.; Sen, A. Macromolecules 2002, 35, 8978 https://doi.org/10.1021/ma020933a
  13. Zhao, C. T.; Ribeiro, M. do R.; Portela, M. F. J. Mol. Catal. A: Chemical 2002, 185, 81 https://doi.org/10.1016/S1381-1169(02)00133-4
  14. Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem. Int. Ed. 1999, 38, 428 https://doi.org/10.1002/(SICI)1521-3773(19990215)38:4<428::AID-ANIE428>3.0.CO;2-3
  15. Mecking, S. Angew. Chem. Int. Ed. 2001, 40, 534 https://doi.org/10.1002/1521-3773(20010202)40:3<534::AID-ANIE534>3.0.CO;2-C
  16. Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169 https://doi.org/10.1021/cr9804644
  17. Mecking, S. Coord. Chem. Rev. 2000, 203, 325 https://doi.org/10.1016/S0010-8545(99)00229-5
  18. Male, N. A. H.; Thornton-Pett, M.; Bochmann, M. J. Chem. Soc., Dalton Trans. 1997, 2487
  19. Kooistra, T. M.; Hekking, K. F. W.; Knijnenburg, Q.; de Bruin, B.; Budzelaar, P. H. M.; de Gelder, R.; Smits, J. M. M.; Gal, A. W. Eur. J. Inorg. Chem. 2003, 648
  20. Borkar, S.; Saxena, P. K. Polym. Bull. 2000, 44, 167 https://doi.org/10.1007/s002890050588
  21. Bistovsek, G. J. P.; Baugh, S. P. D.; Hoarau, O.; Gibson, V. C.; Wass, D. F.; White, A. J. P.; Williams, D. J. Inorg. Chim. Acta 2003, 345, 279 https://doi.org/10.1016/S0020-1693(02)01293-8
  22. Lee, S. A.; Shin, K. Y.; Park, B. J.; Choi, M. K.; Lee, I. M. Bull. Korean Chem. Soc. 2006, 27(4), 475 https://doi.org/10.5012/bkcs.2006.27.4.475
  23. Chapman, R. S.; Stephens, F. S.; Vagg, R. S. Inorg. Chim. Acta 1981, 52, 161. (for $H_{2}$bpb 4) https://doi.org/10.1016/S0020-1693(00)88591-6
  24. Jain, S. L.; Bhattacharyya, P.; Milton, H. L.; Slawin, A. M. Z.; Crayston, J. A.; Woollins, J. D. Dalton Trans. 2004, 862. (for $H_{2}$Mebpb 5)
  25. Lee, S. J.; Lee, J. Y.; Kim, C.; Nam, W.; Kim, Y. Acta Cryst. 2002, E58, m191. (for $H_{2}Me_{2}$bpb 6)
  26. Lee, S. J.; Lee, J. Y.; Yang, H. W.; Kim, C.; Nam, W.; Kim, Y. Acta Cryst. 2002, E58, m313. (for $H_{2}$bpc 3)
  27. Stephens, F.; Vagg, R. S. Inorg. Chim. Acta 1986, 120, 165 https://doi.org/10.1016/S0020-1693(00)86104-6
  28. Shoner, S. C.; Olmstead, M. M.; Kovacs, J. A. Inorg. Chem. 1994, 33, 7 https://doi.org/10.1021/ic00079a004
  29. Bugella-Atamirano, E.; Gonzales-Perez, J. M.; Choquesillo-Lazarte, D.; Carballo, R.; Castineiras, A.; Niclos- Gutierrez, J. Inorg. Chem. Commun. 2002, 5, 727 https://doi.org/10.1016/S1387-7003(02)00552-X
  30. Broring, M.; Brandt, C. D. Chem. Commun. 2003, 2156
  31. Yamamoto, T.; Kohara, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1981, 54, 2010 https://doi.org/10.1246/bcsj.54.2010
  32. Yamamoto, T.; Kohara, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1982, 55, 325 https://doi.org/10.1246/bcsj.55.325
  33. Schmidt, F. K.; Ratovskii, G. V.; Dmitrieva, T. V.; Iveleva, I. N.; Borodko, Yu. G. J. Organomet. Chem. 1983, 256, 309 https://doi.org/10.1016/S0022-328X(00)99208-8
  34. Pozdeeva, A. A.; Dzhemilev, U. M.; Popod'ko, N. R.; Khusnutdinov, R. I.; Zhdanov, S. I.; Tolstikov, G. A. J. Organomet. Chem. 1989, 367, 205 https://doi.org/10.1016/0022-328X(89)87220-1
  35. Tritto, I.; Sacchi, M. C.; Locatelli, P.; Li, S. X. Macromol. Chem. Phys. 1996, 197, 1537 https://doi.org/10.1002/macp.1996.021970429
  36. Zakharov, I. I.; Zakharov, V. A.; Pptapov, A. G.; Zhidomirov, G. M. Macromol. Theory Simulation 1999, 8(3), 272 https://doi.org/10.1002/(SICI)1521-3919(19990501)8:3<272::AID-MATS272>3.0.CO;2-E
  37. Hansson, S.; Norrby, P. O.; Sjögren, M. P. T.; Kermark, B.; Cucciolito, M. E.; Giordano, F.; Vitagliano, A. Organometallics 1993, 12, 4940 https://doi.org/10.1021/om00036a038

Cited by

  1. Steric and Electronic Effects of Tetradentate Nickel(II) and Palladium(II) Complexes toward the Vinyl Polymerization of Norbornene vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.1884
  2. New tetradentate N,N,N,N-chelating α-diimine ligands and their corresponding zinc and nickel complexes: synthesis, characterisation and testing as olefin polymerisation catalysts vol.40, pp.13, 2011, https://doi.org/10.1039/c0dt01308k
  3. Polymerisation of Norbornene Catalysed by Highly Active Tetradentate Chelated α-Diimine Nickel Complexes pp.10221352, 2011, https://doi.org/10.1002/macp.201000612
  4. Synthesis, X-ray structure, electrochemistry, and theoretical studies of palladium(II) complex with a tetradentate bis(quinoline-2-carboxamide) ligand vol.9, pp.1, 2012, https://doi.org/10.1007/s13738-011-0008-9
  5. Robust and Efficient Amide-Based Nonheme Manganese(III) Hydrocarbon Oxidation Catalysts: Substrate and Solvent Effects on Involvement and Partition of Multiple Active Oxidants vol.17, pp.26, 2011, https://doi.org/10.1002/chem.201003202
  6. Amide-Based Nonheme Cobalt(III) Olefin Epoxidation Catalyst: Partition of Multiple Active Oxidants CoVO, CoIVO, and CoIIIOO(O)CR vol.18, pp.19, 2012, https://doi.org/10.1002/chem.201103916
  7. Palladium(ii) complexes with pentafluorophenyl ligands: structures, C6F5 fluxionality by 2D-NMR studies and pre-catalysts for the vinyl addition polymerization of norbornene vol.39, pp.15, 2010, https://doi.org/10.1039/b925674a
  8. Pd(II) polymeric compounds directed by intermolecular C–H⋯X–C interactions (X=F, Cl): Suzuki–Miyaura cross-coupling catalytic activity by a novel N4-type saturated Pd complex vol.26, pp.7, 2006, https://doi.org/10.1016/j.poly.2006.11.020
  9. Steric effect on construction of Cu(II) complexes with pyridine carboxamide ligands vol.885, pp.1, 2006, https://doi.org/10.1016/j.molstruc.2007.10.006
  10. High catalytic activities in the norbornene polymerization with neutral palladium complexes containing N4-type tetradentate chelating ligands vol.362, pp.14, 2006, https://doi.org/10.1016/j.ica.2009.08.026
  11. Steric effect on construction of extended architectures of Ni(II) complexes directed by intermolecular C-H...F and C-H...O interactions vol.51, pp.5, 2006, https://doi.org/10.1007/s10947-010-0140-x
  12. Nickel N‐heterocyclic carbene complexes in the vinyl polymerization of norbornene vol.25, pp.1, 2006, https://doi.org/10.1002/aoc.1714
  13. Reactivity of a Nickel(II) Bis(amidate) Complex with meta‐Chloroperbenzoic Acid: Formation of a Potent Oxidizing Species vol.21, pp.42, 2006, https://doi.org/10.1002/chem.201501841