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Cobalt(III) Complexes of Various Salen-Type Ligand Bearing Four Quaternary Ammonium Salts and Their Reactivity for CO2/Epoxide Copolymerization

  • Kim, Bo-Eun (Department of Molecular Science and Technology, Ajou University) ;
  • Varghese, Jobi Kodiyan (Department of Molecular Science and Technology, Ajou University) ;
  • Han, Yong-Gyu (Department of Molecular Science and Technology, Ajou University) ;
  • Lee, Bun-Yeoul (Department of Molecular Science and Technology, Ajou University)
  • Published : 2010.04.20

Abstract

Ligand variation was carried out on a cobalt(III) complex of Salen-type ligand comprised of 1,2-cyclohexenediamine and salicylaldehyde bearing a methyl substituent on 3-position and -[$CMe(CH_2CH_2CH_2N^+Bu_3)_2$] on 5-position, which is a highly active catalyst for $CO_2$/propylene oxide copolymerization. Replacement of the methyl substituent with bulky isopropyl group resulted in alteration of the binding mode, consequently lowering turnover frequency significantly. Replacement with an ethyl group preserved binding mode and activity. Replacement of the tributylammonium unit with trihexylammonium or trioctylammonium, or replacement of 1,2-cyclohexenediamino unit with -$NC(Me)_2CH_2N$- decreased activity, even though the binding mode was unaltered.

Keywords

References

  1. S, S.; Min, J. K.; Seong, J. E.; Na, S. J.; Lee, B. Y. Angew. Chem., Int. Ed. 2008, 47, 7306. https://doi.org/10.1002/anie.200801852
  2. Seong, J. E.; Na, S. J.; Cyriac,A.; Kim, B.-W.; Lee, B. Y. Macromolecules 2010, 43, ASAP(DOI: 10.1021/ma902162n).
  3. Liu, B.; Chen, L.; Zhang, M.; Yu, A. Macromol. Rapid Commun. 2002, 23, 881. https://doi.org/10.1002/1521-3927(20021001)23:15<881::AID-MARC881>3.0.CO;2-C
  4. Hongfa, C.; Tian, J.; Andreatta, J.; Darensbourg,D. J.; Bergbreiter, D. E. Chem. Commun. 2008, 975.
  5. Luinstra, G. A. Polym. Rev. 2008, 48, 192. https://doi.org/10.1080/15583720701834240
  6. Coates,G. W.; Moore, D. R. Angew. Chem., Int. Ed. 2004, 43, 6618. https://doi.org/10.1002/anie.200460442
  7. Darensbourg, D. J. Chem. Rev. 2007, 107, 2388. https://doi.org/10.1021/cr068363q
  8. Kember, M. R.; Knight, P. D.; Reung, P. T. R.; Williams, C.K. Angew. Chem., Int. Ed. 2009, 48, 931. https://doi.org/10.1002/anie.200803896
  9. Ren, W.-M.; Liu,Z.-W.; Wen, Y.-Q.; Zhang, R.; Lu, X.-B. J. Am. Chem. Soc. 2009,131, 11509. https://doi.org/10.1021/ja9033999
  10. Noh, E. K.; Na, S. J.; S, S.; Kim, S.-W.; Lee, B.Y. J. Am. Chem. Soc. 2007, 129, 8082. https://doi.org/10.1021/ja071290n
  11. Lee, B. Y.; Kwon, H.Y.; Lee, S. Y.; Na, S. J.; Han, S.-i.; Yun, H.; Lee, H.; Park, Y.-W.J. Am. Chem. Soc. 2005, 127, 3031. https://doi.org/10.1021/ja0435135
  12. Bok, T.; Yun, H.; Lee, B. Y. Inorg. Chem. 2006, 45, 4228. https://doi.org/10.1021/ic060060r
  13. Xiao, Y.; Wang, Z.; Ding, K.Chem. Eur. J. 2005, 11, 3668. https://doi.org/10.1002/chem.200401159
  14. Piesik, D. F.-J.; Range, S.; Harder,S. Organometallics 2008, 27, 6178. https://doi.org/10.1021/om800597f
  15. Na, S. J.; S, S.; Cyriac, A.; Kim, B. E.; Yoo, J.; Kang, Y. K.;Han, S. J.; Lee, C.; Lee, B. Y. Inorg. Chem. 2009, 48, 10455. https://doi.org/10.1021/ic901584u
  16. Yoo, J.; Na, S. J.; Park, H. C.; Cyriac, A.; Lee, B. Y. Dalton Trans.2010, DOI: 10.1039/b920992a.
  17. Min, J.; Seong, J. E.; Na, S. J.; Cyriac, A.; Lee, B. Y. Bull. Korean Chem. Soc. 2009, 30, 745. https://doi.org/10.5012/bkcs.2009.30.3.745
  18. Hansen, T. V.; Skattebcal, L. Tetrahedron Lett. 2005, 46, 3829. https://doi.org/10.1016/j.tetlet.2005.03.193
  19. Lu, X.-B.; Shi, L.; Wang, Y.-M.; Zhang, R.; Zhang, Y.-J.; Peng,X.-J.; Zhang, Z.-C.; Li, B. J. Am. Chem. Soc. 2006, 128, 1664. https://doi.org/10.1021/ja056383o

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