Scandium half-metallocene-catalyzed syndiospecific styrene polymerisation and styrene-ethylene copolymerization: Unprecedented incorporation of syndiotactic styrene-styrene sequences in styrene-ethylene copolymers

Journal of the American Chemical Society

Volumn 126, Issue 43, 2004, Pages 13910-13911

  Luo, Yunjie ^a   Baldamus, Jens ^a   Hou, Zhaomin ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMER; ETHYLENE DERIVATIVE; LANTHANIDE; SCANDIUM; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; POLYMERIZATION; SYNTHESIS;

EID: 7444228127     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046063p     Document Type: Article

References (50)

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7. For examples of group 4 metal-catalyzed styrene/ethylene copolymerization, see: (a) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598 and references therein. (b) Chum, P. S.; Kruper, W. J.; Guest, M. J. Adv. Mater. 2000, 12, 1759-1767. (c) Grassi, A.; Caprio, M.; Zambelli, A.; Bowen, D. E. Macromolecules 2000, 33, 8130-8135. (d) Chu, P. P.; Tseng, H. S.; Chen, Y. P.; Yu, D. D. Polymer 2000, 41, 8271-8281. (e) Caporaso, L.; Izzo, L.; Sisti, I.; Oliva, L. Macromolecules 2002, 35, 4866-4870. (f) Nomura, K.; Okumura, H.; Komatsu, T.; Naga, N. Macromolecules 2002, 35, 5388-5395. (g) Capacchione, C.; D'Acunzi, M.; Motta, O.; Oliva, L.; Proto, A.; Okuda, J. Macromol. Chem. Phys. 2004, 205, 370-373. (h) Noh, S. K.; Lee, M. J.; Kum, D. H.; Kim, K.; Lyoo, W. S.; Lee, D. H. J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 1712-1723. (i) Guo, N.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 6542-6543.
8. For examples of group 4 metal-catalyzed styrene/ethylene copolymerization, see: (a) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598 and references therein. (b) Chum, P. S.; Kruper, W. J.; Guest, M. J. Adv. Mater. 2000, 12, 1759-1767. (c) Grassi, A.; Caprio, M.; Zambelli, A.; Bowen, D. E. Macromolecules 2000, 33, 8130-8135. (d) Chu, P. P.; Tseng, H. S.; Chen, Y. P.; Yu, D. D. Polymer 2000, 41, 8271-8281. (e) Caporaso, L.; Izzo, L.; Sisti, I.; Oliva, L. Macromolecules 2002, 35, 4866-4870. (f) Nomura, K.; Okumura, H.; Komatsu, T.; Naga, N. Macromolecules 2002, 35, 5388-5395. (g) Capacchione, C.; D'Acunzi, M.; Motta, O.; Oliva, L.; Proto, A.; Okuda, J. Macromol. Chem. Phys. 2004, 205, 370-373. (h) Noh, S. K.; Lee, M. J.; Kum, D. H.; Kim, K.; Lyoo, W. S.; Lee, D. H. J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 1712-1723. (i) Guo, N.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 6542-6543.
9. For examples of group 4 metal-catalyzed styrene/ethylene copolymerization, see: (a) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598 and references therein. (b) Chum, P. S.; Kruper, W. J.; Guest, M. J. Adv. Mater. 2000, 12, 1759-1767. (c) Grassi, A.; Caprio, M.; Zambelli, A.; Bowen, D. E. Macromolecules 2000, 33, 8130-8135. (d) Chu, P. P.; Tseng, H. S.; Chen, Y. P.; Yu, D. D. Polymer 2000, 41, 8271-8281. (e) Caporaso, L.; Izzo, L.; Sisti, I.; Oliva, L. Macromolecules 2002, 35, 4866-4870. (f) Nomura, K.; Okumura, H.; Komatsu, T.; Naga, N. Macromolecules 2002, 35, 5388-5395. (g) Capacchione, C.; D'Acunzi, M.; Motta, O.; Oliva, L.; Proto, A.; Okuda, J. Macromol. Chem. Phys. 2004, 205, 370-373. (h) Noh, S. K.; Lee, M. J.; Kum, D. H.; Kim, K.; Lyoo, W. S.; Lee, D. H. J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 1712-1723. (i) Guo, N.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 6542-6543.
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12. For examples of group 4 metal-catalyzed styrene/ethylene copolymerization, see: (a) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598 and references therein. (b) Chum, P. S.; Kruper, W. J.; Guest, M. J. Adv. Mater. 2000, 12, 1759-1767. (c) Grassi, A.; Caprio, M.; Zambelli, A.; Bowen, D. E. Macromolecules 2000, 33, 8130-8135. (d) Chu, P. P.; Tseng, H. S.; Chen, Y. P.; Yu, D. D. Polymer 2000, 41, 8271-8281. (e) Caporaso, L.; Izzo, L.; Sisti, I.; Oliva, L. Macromolecules 2002, 35, 4866-4870. (f) Nomura, K.; Okumura, H.; Komatsu, T.; Naga, N. Macromolecules 2002, 35, 5388-5395. (g) Capacchione, C.; D'Acunzi, M.; Motta, O.; Oliva, L.; Proto, A.; Okuda, J. Macromol. Chem. Phys. 2004, 205, 370-373. (h) Noh, S. K.; Lee, M. J.; Kum, D. H.; Kim, K.; Lyoo, W. S.; Lee, D. H. J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 1712-1723. (i) Guo, N.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 6542-6543.
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33. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
34. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
35. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
36. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
37. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
38. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
39. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
40. For examples of olefin polymerization by cationic rare earth metal species, see: (a) Hajela, S.; Schaefer, W. P.; Bercaw, J. E. J. Organomet. Chem. 1997, 532, 45-53. (b) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 9078-9079. (c) Christopher, J. N.; Squire, L. R.; Canich, J. A. M.; Shaffer, T. D. WO 00/18808, 2000. (d) Kaita, S.; Hou, Z.; Wakatsuki, Y. Macromolecules 2001, 34, 1539-1541. (e) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2001, 637-638. (f) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133. (g) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522-523. (h) Kaita, S.; Hou, Z.; Nishiura, M.; Doi, Y.; Kurazumi, J.; Horiguchi, A.; Wakatsuki, Y. Macromol. Rapid Commun. 2003, 24, 180-184. (i) Kaita, S.; Takeguchi, Y.; Hou, Z.; Nishiura, M.; Doi, Y.; Wakatsuki, Y. Macromolecules 2003, 36, 7923-7926. (j) Arndt, S.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 2003, 42, 5075-5079.
41. See Supporting Information for experimental details.
42. 2(THF) toward styrene polymerization was mentioned previously. See: Hultzsch, K. C.; Spaniol, T. P.; Okuda, J. Angew. Chem., Int. Ed. 1999, 38, 227-230.
43. 5Cl. An attempt to treat the cationic Sc species with THF resulted in the polymerization of THF.
44. Coates, G. W. Chem. Rev. 2000, 100, 1223-1252.
45. 4] would result in formation of atactic polystyrene.
46. These results are also in sharp contrast with what was observed previously for other rare earth metal catalysts, which all gave atactic polystyrenes. For examples, see: (a) Voth, P.; Arndt, S.; Spaniol, T. P.; Okuda, J.; Ackerman, L. J.; Green, M. L. H. Organometallics 2003, 22, 65-76. (b) Luo, Y. J.; Yao, Y. M.; Shen, Q. Macromolecules 2002, 35, 8670-8671. (c) Tanaka, K.; Furo, M.; Ihara, E.; Yasuda, H. J. Polym. Sci. A: Polym. Chem. 2001, 39, 1382-1390. (d) Hultzsch, K. C.; Voth, P.; Beckerle, K.; Spaniol, T. P.; Okuda, J. Organometallics 2000, 19, 228-243. (e) Zhang, Y. G.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 939-941. See also refs 4a,b and 6e.
47. These results are also in sharp contrast with what was observed previously for other rare earth metal catalysts, which all gave atactic polystyrenes. For examples, see: (a) Voth, P.; Arndt, S.; Spaniol, T. P.; Okuda, J.; Ackerman, L. J.; Green, M. L. H. Organometallics 2003, 22, 65-76. (b) Luo, Y. J.; Yao, Y. M.; Shen, Q. Macromolecules 2002, 35, 8670-8671. (c) Tanaka, K.; Furo, M.; Ihara, E.; Yasuda, H. J. Polym. Sci. A: Polym. Chem. 2001, 39, 1382-1390. (d) Hultzsch, K. C.; Voth, P.; Beckerle, K.; Spaniol, T. P.; Okuda, J. Organometallics 2000, 19, 228-243. (e) Zhang, Y. G.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 939-941. See also refs 4a,b and 6e.
48. These results are also in sharp contrast with what was observed previously for other rare earth metal catalysts, which all gave atactic polystyrenes. For examples, see: (a) Voth, P.; Arndt, S.; Spaniol, T. P.; Okuda, J.; Ackerman, L. J.; Green, M. L. H. Organometallics 2003, 22, 65-76. (b) Luo, Y. J.; Yao, Y. M.; Shen, Q. Macromolecules 2002, 35, 8670-8671. (c) Tanaka, K.; Furo, M.; Ihara, E.; Yasuda, H. J. Polym. Sci. A: Polym. Chem. 2001, 39, 1382-1390. (d) Hultzsch, K. C.; Voth, P.; Beckerle, K.; Spaniol, T. P.; Okuda, J. Organometallics 2000, 19, 228-243. (e) Zhang, Y. G.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 939-941. See also refs 4a,b and 6e.
49. These results are also in sharp contrast with what was observed previously for other rare earth metal catalysts, which all gave atactic polystyrenes. For examples, see: (a) Voth, P.; Arndt, S.; Spaniol, T. P.; Okuda, J.; Ackerman, L. J.; Green, M. L. H. Organometallics 2003, 22, 65-76. (b) Luo, Y. J.; Yao, Y. M.; Shen, Q. Macromolecules 2002, 35, 8670-8671. (c) Tanaka, K.; Furo, M.; Ihara, E.; Yasuda, H. J. Polym. Sci. A: Polym. Chem. 2001, 39, 1382-1390. (d) Hultzsch, K. C.; Voth, P.; Beckerle, K.; Spaniol, T. P.; Okuda, J. Organometallics 2000, 19, 228-243. (e) Zhang, Y. G.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 939-941. See also refs 4a,b and 6e.
50. These results are also in sharp contrast with what was observed previously for other rare earth metal catalysts, which all gave atactic polystyrenes. For examples, see: (a) Voth, P.; Arndt, S.; Spaniol, T. P.; Okuda, J.; Ackerman, L. J.; Green, M. L. H. Organometallics 2003, 22, 65-76. (b) Luo, Y. J.; Yao, Y. M.; Shen, Q. Macromolecules 2002, 35, 8670-8671. (c) Tanaka, K.; Furo, M.; Ihara, E.; Yasuda, H. J. Polym. Sci. A: Polym. Chem. 2001, 39, 1382-1390. (d) Hultzsch, K. C.; Voth, P.; Beckerle, K.; Spaniol, T. P.; Okuda, J. Organometallics 2000, 19, 228-243. (e) Zhang, Y. G.; Hou, Z.; Wakatsuki, Y. Macromolecules 1999, 32, 939-941. See also refs 4a,b and 6e.