Synthesis, characterization, and MMA polymerization activity of tetrahedral Co (II) complex bearing N, N-bis(1-pyrazolyl)methyl ligand based on aniline moiety

Inorganic Chemistry Communications

Volumn 14, Issue 1, 2011, Pages 189-193

  Yang, Minkyu ^a   Park, Won Jin ^a   Yoon, Keun Byoung ^a   Jeong, Jong Hwa ^a   Lee, Hyosun ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Methyl methacrylate; N N bis(1 H Pyrazole 1 yl); PMMA; Tetrahedral Co (II) complex

Indexed keywords

EID: 78651342304     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2010.10.019     Document Type: Article

References (64)

1. C. Amort, M. Malaun, A. Krajete, H. Kopacka, K. Wurst, M. Christ, D. Lilge, M.O. Kristen, and B. Bildstein Appl. Organomet. Chem. 16 2002 506
2. C. Vedder, F. Schaper, H.-H. Brintzinger, M. Kettunen, S. Babik, and G. Fink Eur. J. Inorg. Chem. 2005 1071
3. L.K. Johnson, C.M. Killian, and M. Brookhart J. Am. Chem. Soc. 117 1995 6414
4. F. Speiser, P. Braunstein, and L. Saussine Acc. Chem. Res. 38 2005 784
5. G.J.P. Britovsek, S. Mastroianni, G.A. Solan, S.P.D. Baugh, C. Redshaw, V.C. Gibson, A.J.P. White, D.J. Williams, and M.R.J. Elsegood Chem. Eur. J. 6 2000 2221
6. S.A. Svejda, and M. Brookhart Organometallics 18 1999 65
7. D. Takeuchi, R. Matsuura, and K. Osakada Macromol. Rapid Commun. 29 2008 1932
8. Y. Chen, R. Chen, C. Qian, X. Dong, and J. Sun Organometallics 22 2003 4312
9. L. Xiao, R. Gao, M. Zhang, Y. Li, X. Cao, and W.-H. Sun Organometallics 28 2009 2225
10. K. Yliheikkilä, K. Lappalainen, P.M. Castro, K. Ibrahim, A. Abu-Surrah, M. Leskelä, and T. Repo Eur. Polym. J. 42 2006 92
11. B.L. Small, and M. Brookhart Macromolecules 32 1999 2120
12. D. Zabel, A. Schubert, G. Wolmershäuser, R.L. Jones Jr., and W.R. Thiel Eur. J. Inorg. Chem. 2008 3648
13. K.P. Tellmann, V.C. Gibson, A.J.P. White, and D.J. Williams Organometallics 24 2005 280
14. B.L. Small, and M. Brookhart J. Am. Chem. Soc. 120 1998 7143
15. B.L. Small, M. Brookhart, and A.M.A. Bennett J. Am. Chem. Soc. 120 1998 4049
16. G.J.P. Britovsek, V.C. Gibson, B.S. Kimberley, P.J. Maddox, S.J. McTavish, G.A. Solan, A.J.P. White, and D.J. Williams Chem. Commun. 1998 849
17. R. Cowdell, C.J. Davies, S.J. Hilton, J.-D. Maréchal, G.A. Solan, O. Thomas, and J. Fawcett Dalton Trans. 2004 3231
18. G.J.P. Britovsek, V.C. Gibson, O.D. Hoarau, S.K. Spitzmesser, A.J.P. White, and D.J. Williams Inorg. Chem. 42 2003 3454
19. G.J.P. Britovsek, V.C. Gibson, S. Mastroianni, D.C.H. Oakes, C. Redshaw, G.A. Solan, A.J.P. White, and D.J. Williams Eur. J. Inorg. Chem. 2001 431
20. L.G. Furlan, M.P. Gil, and O.L. Casagrande Jr. Macromol. Rapid Commun. 21 2000 1054
21. K. Li, J. Darkwa, I.A. Guzei, and S.F. Mapolie J. Organomet. Chem. 660 2002 108
22. S. Tsuji, D.C. Swenson, and R.F. Jordan Organometallics 18 1999 4758
23. T.G. Schenck, J.M. Downes, C.R.C. Milne, P.B. Mackenzie, H. Boucher, J. Whelan, and B. Bosnich Inorg. Chem. 24 1985 2334
24. L.L. de Oliveira, R.R. Campedelli, M.C.A. Kuhn, J.-F. Carpentier, and O.L. Casagrande Jr. J. Mol. Catal. A Chem. 288 2008 58
25. Z. Zhang, D. Cui, and A.A. Trifonov Eur. J. Inorg. Chem. 2010 2861
26. C. Lansalot-Matras, F. Bonnette, E. Mignard, and O. Lavastre J. Organomet. Chem. 693 2008 393
27. B. Lian, C.M. Thomas, O.L. Casagrande Jr., C.W. Lehmann, T. Roisnel, and J.-F. Carpentier Inorg. Chem. 46 2007 328
28. S. Scheuer, J. Fischer, and J. Kress Organometallics 14 1995 2627
29. D.P. Long, and P.A. Bianconi J. Am. Chem. Soc. 118 1996 12453
30. H. Nakazawa, S. Ikai, K. Imaoka, Y. Kai, and T. Yano J. Mol. Catal. A:Chem. 132 1998 33
31. S. Murtuza, O.L. Casagrande Jr., and R.F. Jordan Organometallics 21 2002 1882
32. S. Trofimenko Chem. Rev. 72 1972 497
33. S. Trofimenko Chem. Rev. 93 1993 943
34. R. Mukherjee Coord. Chem. Rev. 203 2000 151
35. I.N. Stepanenko, B. Cebrián-Losantos, V.B. Arion, A.A. Krokhin, A.A. Nazarov, and B.K. Keppler Eur. J. Inorg. Chem. 2007 400
36. M. Daoudi, N.B. Larbi, A. Kerbal, B. Bennani, J.-P. Launay, J. Bonvoisin, T.B. Hadda, and P.H. Dixneuf Tetrahedron 62 2006 3123
37. J. Pons, A. Chadghan, A. Alvarez-Larena, J.F. Piniella, and J. Ros Inorg. Chim. Acta 324 2001 342
38. R. Touzani, A. Ramdani, T. Ben-Hadda, S.E. Kadiri, O. Maury, H.L. Bozec, and P.H. Dixneuf Synth. Commun. 31 2001 1315
39. A.R. Karam, E.L. Catarí, F. López-Linares, G. Agrifoglio, C.L. Albano, A. Díaz-Barrios, T.E. Lehmann, S.V. Pekerar, L.A. Albornoz, R. Atencio, T. González, H.B. Ortega, and P. Joskowics Appl. Catal., A 280 2005 165
40. N. Ajellal, M.C.A. Kuhn, A.D.G. Boff, M. Hörner, C.M. Thomas, J.-F. Carpentier, and O.L. Casagrande Jr. Organometallics 25 2006 1213
41. S.J. Dougan, M. Melchart, A. Habtemariam, S. Parsons, and P.J. Sadler Inorg. Chem. 45 2006 10882
42. N. Singh, N.K. Sangwan, and K.S. Dhindsa Pest Manag. Sci. 56 2000 284
43. E. Budzisz, U. Krajewska, M. Rozalski, A. Szulawska, M. Czyz, and B. Nawrot Eur. J. Pharmacol. 502 2004 59
44. T.B. Hadda, A.T. Kotchevar, M. Daoudi, B. Bennani, N. Ben Larbi, and A. Kerbal Lett. Drug Des. Discovery 2 2005 584
45. I. Bouabdallah, L.A. M'barek, A. Zyad, A. Ramdani, I. Zidane, and A. Melhaoui Nat. Prod. Res. 20 2006 1024
46. J. Hitzbleck, A.Y. O'Brien, G.B. Deacon, and K. Ruhlandt-Senge Inorg. Chem. 45 2006 10329
47. P.M. van Berkel, W.L. Driessen, R. Hämäläinen, J. Reedijk, and U. Turpeinen Inorg. Chem. 33 1994 5920
48. C. Dowling, V.J. Murphy, and G. Parkin Inorg. Chem. 35 1996 2415
49. A.R. Katritzky, S. Rachwal, and J. Wu Can. J. Chem. 68 1990 446
50. -1): 1453 (w), 1405 (m), 1321 (w), 1302 (m), 1250 (m), 1206 (w), 1190 (m),1169 (s), 1158 (m), 1100 (w), 1083 (w), 1064 (s), 991 (w), 975 (m), 941 (w), 921 (w), 907 (w), 878 (w), 847 (m), 815 (w), 765 (s), 735 (s), 687 (w), 675 (w), 644 (m), 608 (s), 588 (s), 555 (s).
51. 2 = 0.1681.
52. H.L. Blonk, W.L. Driessen, and J. Reedijk Chem. Soc., Dalton Trans 1985 1699
53. S.-C. Sheu, M.-J. Tien, M.-C. Cheng, T.-I. Ho, S.-M. Peng, and Y.-C. Lin J. Chem. Soc., Dalton Trans 1995 3503
54. Q.-Y. Li, X.-Y. Tang, W.-H. Zhang, J. Wang, Z.-G. Ren, H.-X. Li, Y. Zhang, and J.-P. Lang J. Mol. Struct. 879 2008 119
55. G.J.P. Britovsek, M. Bruce, V.C. Gibson, B.S. Kimberley, P.J. Maddox, S. Mastroianni, S.J. McTavish, C. Redshaw, G.A. Solan, S. Strömberg, A.J.P. White, and D.J. Williams J. Am. Chem. Soc. 121 1999 8728
56. N. Zhao, M.J. Van Stipdonk, and D.M. Eichhorn Polyhedron 26 2007 2449
57. I. Kuzu, I. Krummenacher, I.J. Hewitt, Y. Lan, V. Mereacre, A.K. Powell, P. Höfer, J. Harmer, and F. Breher Chem. Eur. J. 15 2009 4350
58. C. Bianchini, G. Giambastiani, G. Mantovani, A. Meli, and D. Mimeau J. Organomet. Chem. 689 2004 1356
59. M.D. Fryzuk, D.B. Leznoff, R.C. Thompson, and S.J. Rettig J. Am. Chem. Soc. 120 1998 10126
60. B.K. Bahuleyan, D. Chandran, C.H. Kwak, C.-S. Ha, and I. Kim Macromol. Res. 18 2008 745
61. J. Li, H. Song, and C. Cui Appl. Organomet. Chem. 24 2010 82
62. X. He, Y. Yao, X. Luo, J. Zhang, Y. Liu, L. Zhang, and Q. Wu Organometallics 22 2003 4952
63. W. Wang, P.A. Stenson, A. Marin-Becerra, J. McMaster, M. Schröder, D.J. Irvine, D. Freeman, and S.M. Howdle Macromolecules 37 2004 6667
64. Representative polymerization procedure of MMA: Methyl methacrylate (MMA) was extracted with 10% sodium hydroxide, washed with water, dried over magnesium sulfate, and distilled over calcium hydride under reduced pressure before use. To a 100-mL Schlenk flask containing [bpmaL]CoCl2 (5.8 mg, 15.0 μmol) in toluene (1 mL) was added MMAO (modified methylaluminoxane, 6.9 wt% in toluene, 3.25 mL, [MMAO]0/[Catalyst]0 = 500) under a dry argon atmosphere. After the mixture had been stirred at room temperature for 10 min, it was transferred into MMA (5.0 mL, 47.0 mmol, [MMA]0/[Co (II) catalyst]0 = 3100). Then, the reaction flask was immersed in an oil bath at 60 °C and stirred for 2 h. The resulting polymer was precipitated in methanol (400 mL) and HCl (3 mL) was added with stirring for 10 min. The polymer was filtered and washed with methanol (400 mL × 3) to give PMMA, which was vacuum-dried at 60 °C. Additionally, polymerization was examined at different temperatures (0 °C, 25 °C, 40 °C, 50 °C) with 4a.