Phase-selective solubility of poly(N-alkylacrylamide)s

Journal of the American Chemical Society

Volumn 125, Issue 27, 2003, Pages 8244-8249

  Bergbreiter, David E ^a   Hughes, Reagan ^a   Besinaiz, Jacqueline ^a   Li, Chunmei ^a   Osburn, Philip L ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHASE-SELECTIVE SOLUBILITY;

FLUORESCENCE; HEPTANE; SOLUBILITY; SOLVENTS; ULTRAVIOLET SPECTROSCOPY;

ORGANIC POLYMERS;

ACRYLAMIDE DERIVATIVE; ALCOHOL; HEPTANE; POLY(N ACRYLOXYSUCCINIMIDE); POLY(N ISOPROPYLACRYLAMIDE); POLY(N OCTADECYLACRYLAMIDE); POLYACRYLAMIDE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; FLUORESCENCE SPECTROSCOPY; MISCIBILITY; POLARIZATION; REACTION ANALYSIS; SOLUBILITY; SYNTHESIS; TEMPERATURE DEPENDENCE; ULTRAVIOLET RADIATION;

EID: 0038682508     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0349498     Document Type: Article

References (36)

1. (a) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345-3383.
2. (b) Bergbreiter, D. E. J. Polym. Sci., Polym. Chem. Ed. 2001, 39, 2351-2363.
3. Representative examples where solvent precipitation is used to recover catalysts bound to polymers such as poly(alkene oxide)s, polystyrenes, and chiral polymers can be found in recent reviews: (a) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325-3343.
4. Representative examples where solvent precipitation is used to recover catalysts bound to polymers such as poly(alkene oxide)s, polystyrenes, and chiral polymers can be found in recent reviews: (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546-554.
5. Representative examples where solvent precipitation is used to recover catalysts bound to polymers such as poly(alkene oxide)s, polystyrenes, and chiral polymers can be found in recent reviews: (c) Bergbreiter, D. E. In Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, Germany, 2000; pp 43-80.
6. Representative examples where solvent precipitation is used to recover catalysts bound to polymers such as poly(alkene oxide)s, polystyrenes, and chiral polymers can be found in recent reviews: (d) Fan, O.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385-3465.
7. Malmström, T.; Andersson, C. J. Mol. Catal., A 2000, 157, 79-82.
8. Osburn, P. L.; Bergbreiter, D. E. Prog. Polym. Sci. 2001, 26, 2015-2081.
9. (a) Bergbreiter, D. E.; Caraway, J. W. J. Am. Chem. Soc. 1996, 118, 6092-6093.
10. (b) Huang, X.; Witte, K. L.; Bergbreiter, D. E.; Wong, C. H. Adv. Synth. Catal. 2001, 343, 675-681.
11. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053-6062.
12. Vankelecom, I. F. J. Chem. Rev. 2002, 102, 3779-3810. Sirkar, K. K.; Shanbhag, P. V.; Kowali, A. S. Ind. Eng. Chem. Res. 1999, 38, 3715-3737. Dijkstra, H. P.; van Klink, G. P. M.; van Koten, G. Acc. Chem. Res. 2002, 35, 798-810.
13. Vankelecom, I. F. J. Chem. Rev. 2002, 102, 3779-3810. Sirkar, K. K.; Shanbhag, P. V.; Kowali, A. S. Ind. Eng. Chem. Res. 1999, 38, 3715-3737. Dijkstra, H. P.; van Klink, G. P. M.; van Koten, G. Acc. Chem. Res. 2002, 35, 798-810.
14. Vankelecom, I. F. J. Chem. Rev. 2002, 102, 3779-3810. Sirkar, K. K.; Shanbhag, P. V.; Kowali, A. S. Ind. Eng. Chem. Res. 1999, 38, 3715-3737. Dijkstra, H. P.; van Klink, G. P. M.; van Koten, G. Acc. Chem. Res. 2002, 35, 798-810.
15. van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717-3756.
16. (a) Bergbreiter, D. E.; Liu, Y.-S.; Osburn, P. L. J. Am. Chem. Soc. 1998, 120, 4251-4252.
17. (b) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064.
18. (c) Bergbreiter, D. E.; Osburn, P. L.; Frels, J. D. J. Am. Chem. Soc. 2001, 123, 11105-11106.
19. (d) Mizugaki, T.; Murata, M.; Ooe, M.; Ebitani, K.; Kaneda, K. Chem. Commun. 2002, 52-53.
20. (e) Chiba, K.; Kono, Y.; Kim, S.; Nishimoto, K.; Kitano, Y.; Tada, M. Chem. Commun. 2002, 1766-1767.
21. (f) Köllhofer, A.; Plenio, H. Chem.-Eur. J. 2003, 9, 1416-1425.
22. (g) Bergbreiter, D. E.; Koshti, N.; Franchina, J. G.; Frels, J. D. Angew. Chem., Int. Ed. 2000, 39, 1040-1042.
23. (a) Abatjoglou et al. (Abatjoglou, A. G.; Peterson, R. R.; Bryant, D. R. Chem. Ind. 1996, 68, 133-139) describe such separations as 'phase decantantions' and report how they can be used with low molecular weight catalysts and products.
24. (b) Bergbreiter, D. E.; Osburn, P. L.; Smith, T.; Li, C.; Frels, J. D. J. Am. Chem. Soc. 2003, 125, 6254-6260.
25. (c) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570-1571.
26. (d) Scurto, A. M.; Aki, S. N. V. K.; Brennecke, J. F. J. Am. Chem. Soc. 2002, 124, 10276-10277.
27. The variation in molecular weight distribution is a recognized problem that affects the utility of N-alkylacrylamides in a variety of problems including, for example, drug delivery applications and is one reason more well-defined but more expensive polymers such as dendrimers are of increasing interest; cf. Gillies, E. R.; Frechet, J. M. J. J. Am. Chem. Soc. 2002, 124, 14137-14146.
28. Winnik, F. M. Macromolecules 1990, 23, 233-242.
29. Pollak, A.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 289-291.
30. Taylor, L. D.; Cerankowski, L. D. J. Polym. Sci., Polym. Chem. Ed. 1975, 13, 2551-2570. Schild, H. G. Prog. Polym. Sci. 1992, 17, 163-249.
31. Taylor, L. D.; Cerankowski, L. D. J. Polym. Sci., Polym. Chem. Ed. 1975, 13, 2551-2570. Schild, H. G. Prog. Polym. Sci. 1992, 17, 163-249.
32. Mao, H.; Li, C.; Zhang, Y.; Bergbreiter, D. E.; Cremer, P. S. J. Am. Chem. Soc. 2003, 125, 2850-2851.
33. Stevens, M. P. Polymer Chemistry, An Introduction; Oxford University Press: New York, 1999; pp 38-40.
34. Batz, H. G.; Franzmann, G.; Ringsdorf, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 1103-1104.
35. Mammen, M.; Dahmann, G.; Whitesides, G. M. J. Med. Chem. 1995, 38, 4179-4190.
36. Liu, Y.-S.; Zhao, C.; Bergbreiter, D. E.; Romo, D. J. Org. Chem. 1998, 63, 3471-3473.