Calixarene-core multifunctional initiators for the ruthenium-mediated living radical polymerization of methacrylates

Macromolecules

Volumn 31, Issue 20, 1998, Pages 6762-6768

  Ueda, Jiro ^a   Kamigaito, Masami ^a   Sawamoto, Mitsuo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BLOCK COPOLYMERS; COPOLYMERIZATION; FREE RADICAL POLYMERIZATION; HYDROLYSIS; INITIATORS (CHEMICAL); MOLECULAR WEIGHT; RUTHENIUM; SYNTHESIS (CHEMICAL); TOLUENE;

CALIXARENE; MULTIFUNCTIONAL INITIATORS; SEQUENTIAL BLOCK COPOLYMERIZATION;

POLYMETHYL METHACRYLATES;

EID: 0032491111     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma980608g     Document Type: Article

References (28)

1. This work was presented in part at the following meetings: (a) The 213th National Meeting on the American Chemical Society, San Francisco, CA, April 1997 (Sawamoto, M.; Kamigaito, M. PMSE (Am. Chem. Soc., Div. Polym. Mater.: Sci. and Eng.) 1997, 76, 154) and (b) the 46th Annual Meeting of the Society of Polymer Science, Tokyo, Japan, May 1997; paper 1Pd046 (Ueda, J.; Kamigaito, M.; Sawamoto, M. Polym. Prepr. Jpn. 1997, 46 (2), 147).
2. This work was presented in part at the following meetings: (a) The 213th National Meeting on the American Chemical Society, San Francisco, CA, April 1997 (Sawamoto, M.; Kamigaito, M. PMSE (Am. Chem. Soc., Div. Polym. Mater.: Sci. and Eng.) 1997, 76, 154) and (b) the 46th Annual Meeting of the Society of Polymer Science, Tokyo, Japan, May 1997; paper 1Pd046 (Ueda, J.; Kamigaito, M.; Sawamoto, M. Polym. Prepr. Jpn. 1997, 46 (2), 147).
3. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
4. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
5. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
6. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
7. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
8. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
9. For reviews on synthesis of star polymers by ionic living polymerizations, see: (a) Bauer, B. J.; Fetters, L. J. Rubber Chem. Technol. 1978, 51, 406. (b) Rempp, P.; Franta, E. Adv. Polym. Sci. 1984, 58, 1. (c) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983; pp 221-232. (d) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996; pp 333-368. (e) Simms, J. A.; Spinelli, H. J. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; pp 379-391. (f) Sawamoto, M. In Cationic Polymerization; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; pp 412-420. (g) Sawamoto, M.; Kamigaito, M. In New Methods of Polymer Synthesis; Ebdon, J. R.; Eastmond, G. C., Eds.; Blackie: Glasgow, 1995; Vol. 2, pp 37-68.
10. Sogah, D. Y.; Hertler, W. R.; Webster, O. W.; Cohen, G. M. Macromolecules 1988, 20, 1473.
11. Zhu, Z.; Rider, J.; Yang, C. Y.; Gilmartin, M. E.; Wnek, G. E. Macromolecules 1992, 25, 7330.
12. Simms, J. A.; Spinelli, H. J. J. Coat. Technol. 1987, 59, 125.
13. Hatada, K.; Kitayama, T. In Macromolecular Design of Polymeric Materials; Hatada, K., Kitayama, T., Vogl, O., Eds.; Marcel Dekker: New York, 1997; p 154.
14. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
15. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
16. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
17. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
18. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
19. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
20. For recent reviews on living/controlled radical polymerizations, see: (a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (b) Davis, T. P.; Kukulj, D.; Haddleton, D. M.; Maloney, D. R. Trends Polym. Sci. 1995, 3, 365. (c) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (d) Sawamoto, M.; Kamigaito, M. Trends Polym. Sci. 1996, 4, 371. (e) Colombani, D. Prog. Polym. Sci. 1997, 22, 1649. (f) Hawker, C. J. Acc. Chem. Res. 1997, 30, 373. (g) Sawamoto, M.; Kamigaito, M. Polymer Synthesis (Materials Science and Technology Series); Schlüter, A.-D., Ed.; VCH-Wiley: Weinheim, Germany, Chapter 6, in press.
21. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
22. Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185.
23. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721.
24. Wang, J.-S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
25. Ueda, J.; Matsuyama, M.; Kamigaito, M.; Sawamoto, M. Macromolecules 1998, 31, 557.
26. Hawker, C. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1456.
27. For a review on calixarenes, see: Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161.
28. Jacob, S.; Majoros, I.; Kennedy, J. P. Macromolecules 1996, 29, 8631.