Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Novel Pd Catalysts with β-Diketiminates for Homopolymerization of Functionalized Norbornene Derivatives in Water/Organic Mixed Solvents

  • Received : 2013.06.06
  • Accepted : 2013.06.22
  • Published : 2013.09.20
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Abstract

Polynorbornenes prepared by vinyl addition pathway are known to have some desirable characteristics for wider application but they have some critical drawbacks such as brittleness, poor solubility and adhesion. In order to improve these drawbacks, extensive research for the successful homo- and copolymerization of polar functionalized norbornene with olefin has been carried out. Even though considerable advance has been achieved in the polymerization of polar functionalized monomers, successful catalytic systems for the homopolymerization of polar functionalized norbornene are rare. In this study, a novel successful catalytic system for the polymerization of polar functionalized norborene is proposed. This system employs Pd ${\beta}$-diketiminate/borate cocatalyst in water/organic mixed solvents and it is unique due to introduction of water as a component of solvents. Polymers obtained in this study show high Mw with narrow PDI. Effects of several reaction parameters to the polymer activity and properties are investigated and optimal catalytic system are proposed.

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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, 2812.
  2. Yang, H.; Li, Z.; Sun, W. H. J. Mol. Catal. A: Chem. 2003, 206, 23. 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: Chem. 2001, 166, 193. https://doi.org/10.1016/S1381-1169(00)00475-1
  5. Boffa, L. S.; Novak, B. M. Chem. Rev. 2000, 100, 1479. https://doi.org/10.1021/cr990251u
  6. Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283. https://doi.org/10.1021/cr980461r
  7. Reichmanis, E.; Nalamasu, O.; Houlihan, F. M. Acc. Chem. Res. 1999, 32, 659. https://doi.org/10.1021/ar970150n
  8. Nakamura, A.; Ito, S.; Nozaki, K. Chem. Rev. 2009, 109, 5215. https://doi.org/10.1021/cr900079r
  9. Ittel, S. D.; Johnson, I. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169. https://doi.org/10.1021/cr9804644
  10. Drent, E.; van Dijk, R.; van Ginkel, R.; van Oort, B.; Pugh, R. I. Chem. Commun. 2002, 744.
  11. Drent, E.; Pello, D. H.; Jager, W. W. Eur. Pat. Appl. 0.589.587, Mar. 30, 1994.
  12. Chen, Y.; Mandal, S.; Sen, A. Organometallics 2010, 29, 3160. https://doi.org/10.1021/om1003013
  13. Elia, C.; Elyashiv-Barad, S.; Sen, A.; Lopez-Fernandez, R.; Albeniz, A. C.; Espinet, P. Organometallics 2002, 21, 4249. https://doi.org/10.1021/om020435q
  14. Kang, M.; Sen, A. Organometallics 2004, 23, 5396. https://doi.org/10.1021/om049449h
  15. Liu, S.; Borkar S.; Newsham, D.; Yenawar, H.; Sen, A. Organometallics 2007, 26, 210. https://doi.org/10.1021/om0607402
  16. Funk, J. K.; Andes, C. E.; Sen, A. Organometallics 2004, 23, 1680. https://doi.org/10.1021/om049943l
  17. Chen, Y.; Mandal, S.; Sen, A. Organometallics 2010, 29, 3160. https://doi.org/10.1021/om1003013
  18. Ravasio, A.; Boggioni, L.; Tritto, I. Macromolecules 2011, 44, 4180. https://doi.org/10.1021/ma2006427
  19. Tritto, I.; Boggioni, L.; Ravasio, A.; Scalcione, G. Macromol. React. Eng. 2013, 7, 91. https://doi.org/10.1002/mren.201200056
  20. Wang, K.; Chen, Y.; He, X.; Liu, Y.; Zhou, W. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 3304. https://doi.org/10.1002/pola.24767
  21. Tetsuka, H.; Hagiwara, M.; Kaita, S. Polym. J. 2011, 43, 97. https://doi.org/10.1038/pj.2010.99
  22. Zhou, W.; He, X.; Chen, Y.; Chen, M.; Shi, L.; Wu, Q. J. Appl. Polym. Sci. 2011, 120, 2008. https://doi.org/10.1002/app.33305
  23. Huang, R.; He, X.; Chen, Y.; Nie, H.; Zhou, W. Polym. Adv. Tech. 2012, 23, 483. https://doi.org/10.1002/pat.1903
  24. Kaita, S.; Matsushita, K.; Tobita, M.; Maruyama, Y.; Wakatsuki, Y. Macromol. Rapid Commun. 2006, 27, 1752. https://doi.org/10.1002/marc.200600464
  25. Casares, J. A.; Espinet, P.; Salas, G. Organometallics 2008, 27, 3761. https://doi.org/10.1021/om800264a
  26. Xing, Y.; He, X.; Chen, Y.; Nie, H.; Wu, Q. Polym. Bull. 2010, 66(9), 1149.
  27. Pei, L.; Gao, H. J. Mol. Catal. A: Chem. 2011, 336, 94. https://doi.org/10.1016/j.molcata.2011.01.003
  28. Gao, H.; Liu, X.; Pei, L; Wu, Q. J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 1113. https://doi.org/10.1002/polb.21852
  29. Lee, D. W.; Park, S. E.; Cho, K. H.; Kim, Y. S.; Athar, T.; Lee, I. M. Tetrahedron Lett. 2007, 48, 8281. https://doi.org/10.1016/j.tetlet.2007.09.143
  30. Yoon, S. B.; Lee, B. K.; Lee, E. J.; Kye, Y. H.; Lee, I. M. Bull. Korean Chem. Soc. submitted for publication.
  31. Lee, D. H.; Hwang, Y. J.; Yoon, J. S.; Choi, M. K.; Lee, I. M. Bull. Korean Chem. Soc. 2009, 30(3), 636. https://doi.org/10.5012/bkcs.2009.30.3.636
  32. Lee, E. J.; Kim, H. S.; Lee, B. K.; Hwang, W. S.; Sung, I. K.; Lee, I. M. Bull. Korean Chem. Soc. 2012, 33(12), 4131. https://doi.org/10.5012/bkcs.2012.33.12.4131
  33. Vollmerhaus, R.; Rahim, M.; Tomaszewski, R.; Xin, S.; Taylor, N. J.; Collins, S. Organometallics 2000, 19, 2161. https://doi.org/10.1021/om9908027
  34. He, X.; Yao, Y.; Luo, X.; Zhang, J.; Liu, Y.; Zhang, L.; Wu, Q. Organometallics 2003, 22, 4952. https://doi.org/10.1021/om030292n

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