Amphiphilic approach for preparing homopolyrotaxanes of poly(ethylene oxide)

Macromolecules

Volumn 30, Issue 26, 1997, Pages 8139-8152

  Pugh, Coleen ^a   Bae, Jin Young ^a   Scott, Jill R ^b   Wilkins, Charles L ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BENZENE; CROWN ETHERS; MACROMOLECULES; MICELLES; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; PHASE SEPARATION; REACTION KINETICS; TOLUENE;

END CAPPING REACTION; HOMOPOLYROTAXANES;

POLYETHYLENE OXIDES;

EID: 0031353706     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9712155     Document Type: Article

References (81)

1. Rotaxane reviews: (a) Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Amabilino, D. B.; Stoddart, J. F. Chem Rev. 1995, 95, 2725. (c) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 9; Chapter 3. (d) Vogtle, F.; Dunnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451.
2. Rotaxane reviews: (a) Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Amabilino, D. B.; Stoddart, J. F. Chem Rev. 1995, 95, 2725. (c) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 9; Chapter 3. (d) Vogtle, F.; Dunnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451.
3. Rotaxane reviews: (a) Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Amabilino, D. B.; Stoddart, J. F. Chem Rev. 1995, 95, 2725. (c) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 9; Chapter 3. (d) Vogtle, F.; Dunnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451.
4. Rotaxane reviews: (a) Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971. (b) Amabilino, D. B.; Stoddart, J. F. Chem Rev. 1995, 95, 2725. (c) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 9; Chapter 3. (d) Vogtle, F.; Dunnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451.
5. Polyrotaxane reviews: (a) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11. (b) Ogino, H. New J. Chem. 1993, 17, 683. ] (c) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (d) Amabilino, D. B.; Parsons, I. W.; Stoddart, J. F. Trends Polym. Sci. 1994, 2, 146. (e) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208.
6. Polyrotaxane reviews: (a) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11. (b) Ogino, H. New J. Chem. 1993, 17, 683. ] (c) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (d) Amabilino, D. B.; Parsons, I. W.; Stoddart, J. F. Trends Polym. Sci. 1994, 2, 146. (e) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208.
7. Polyrotaxane reviews: (a) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11. (b) Ogino, H. New J. Chem. 1993, 17, 683. ] (c) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (d) Amabilino, D. B.; Parsons, I. W.; Stoddart, J. F. Trends Polym. Sci. 1994, 2, 146. (e) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208.
8. Polyrotaxane reviews: (a) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11. (b) Ogino, H. New J. Chem. 1993, 17, 683. ] (c) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (d) Amabilino, D. B.; Parsons, I. W.; Stoddart, J. F. Trends Polym. Sci. 1994, 2, 146. (e) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208.
9. Polyrotaxane reviews: (a) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11. (b) Ogino, H. New J. Chem. 1993, 17, 683. ] (c) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (d) Amabilino, D. B.; Parsons, I. W.; Stoddart, J. F. Trends Polym. Sci. 1994, 2, 146. (e) Raymo, F. M.; Stoddart, J. F. Trends Polym. Sci. 1996, 4, 208.
10. (a) Ogata, N.; Sanui, K.; Wada, J. J. Polym. Sci., Polym. Lett. Ed. 1976, 14, 459.
11. (b) Maciejewski, M. J. Macromol. Sci.-Chem. 1979, A13, 77.
12. (c) Maciejewski, M.; Gwizdowski, A.; Pezak, P.; Pietrazak, A. J. Macromol. Sci.-Chem. 1979, A13, 87.
13. (d) Maciejewski, M. J. Macromol. Sci.-Chem. 1979, A13,1175.
14. (e) Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1991, 1677.
15. (f) Wenz, G.; Keller, B. Angew. Chem., Int. Ed. Engl. 1992, 37, 197.
16. (g) Shen, Y. X.; Gibson, H. W. Macromolecules 1992, 25, 2058.
17. (h) Shen, Y. X.; Engen, P. T.; Berg, M. A. G.; Merola, J. S.; Gibson, H.W. Macromolecules 1992, 25, 2786.
18. (i) Shen, Y. X.; Xie, D.; Gibson, H. W. J. Am. Chem. Soc. 1994, 116, 537.
19. (j) Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803.
20. (k) Sun, X.; Amabilino, D. B.; Ashton, P. R.; Parsons, I. W.; Stoddart, J. F.; Tolley, M. S. Macromol. Symp. 1994, 77, 191.
21. (l) Loveday, D.; Wilkes, G. L.; Bheda, M. C.; Shen, Y. X.; Gibson, H. W. J. Macromol. Sci., Chem. 1995, A32, 1.
22. (m) Preece, J. A.; Stoddart, J. F. Macromol. Symp. 1995, 98, 527.
23. (n) Marand, E.; Hu, Q.; Gibson, H. W.; Veytsman, B. Macromolecules 1996, 29, 2555.
24. (o) Huff, J.; Preece, J. A.; Stoddart, J. F. Macromol. Symp. 1996, 102, 1.
25. (p) Asakawa, M.; Ashton, P. R.; Brown, G. R.; Hayes, W.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Adv. Mater. 1996, 8, 37.
26. (q) Mason, P. E.; Parsons, I. W.; Tolley, M. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2238.
27. (r) Owen, G. J.; Hodge, P. Chem. Commun. 1997, 11.
28. (s) Gibson, H. W.; Liu, S.; Gong, C.; Ji, Q.; Joseph, E. Macromolecules 1997, 30, 3711.
29. (a) Lipatova, T. E.; Kosyanchuk, L. F.; Gomza, Y. P.; Shilov, V. V.; Lipatov, Y.S. Dokl. Akad. Nauk. SSSR (Engl. Transi.) 1982, 263, 140.
30. (b) Lipatova, T. E.; Kosyanchuk, L. F.; Shilov, V. V.; Gomza, Y. P. Polym. Sci. USSR (Engl. Transi.) 1985, 27, 622.
31. (c) Shaffer, T. D.; Tsay, L.-M. J. Polym. Sci., Polym. Chem. Ed. 1991, 29, 1213.
32. (d) Kern, J.-M.; Sauvage, J.-P.; Bidan, G.; Billon, M.; Divisia-Blohorn, B. Adv. Mater. 1996, 8, 580.
33. (e) Whang, D.; Kim, K. J. Am. Chem. Soc. 1996, 118, 451.
34. (f) Yamaguchi, I.; Osakada, K.; Yamamoto, T. J. Am. Chem. Soc. 1996, 118, 1811.
35. (g) Zhu, S. S.; Carroll, P. J.; Swager, T. M. J. Am. Chem. Soc. 1996, 118, 8713.
36. (h) Whang, D.; Jeon, Y.-M.; Heo, J.; Kim, K. J. Am. Chem. Soc. 1996, 118, 11333.
37. (i) Hoskins, B. F.; Robson, R.; Slizys, D. A. J. Am. Chem. Soc. 1997, 119, 2952.
38. (a) Harada, A. Coord. Chem. Rev. 1996, 148, 115 and references therein,
39. (b) Panova, I. G.; Gerasimov, V. I.; Grokhovskaya, T. E.; Topchieva, I. N. Dokl. Akad. Nauk. SSSR (Engl. Transi.) 1996, 347, 58.
40. (c) Fujita, H.; Ooya, T.; Kurisawa, M.; Mori, H.; Terano, M.; Yui, N. Macromol. Rapid Commun. 1996, 17, 509.
41. Agam, G.; Graiver, D.; Zilkha, A. J. Am. Chem. Soc. 1976, 98, 5206.
42. Kon-no, K. In Surface and Colloid Science; Matijevic, E., Ed.; Plenum Press: New York, 1993; Vol. 15, Chapter 3; and references therein.
43. Brandys, F. A.; Pugh, C. Macromolecules 1997, 30, 8153.
44. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 55, 3195.
45. (a) Jacobson, H.; Stockmayer, W. J. Chem. Phys. 1950, 18, 1600.
46. (b) Jacobson, H.; Beckmann, C. O.; Stockmayer, W. J. Chem. Phys. 1950, 18, 1607.
47. Chenevert, R.; D'Astous, L. J. Heterocycl. Chem. 1986, 23, 1785.
48. (a) Benedict, D. R.; Bianchi, T. A.; Gate, L. A. Synthesis 1979, 428.
49. (b) Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 2169.
50. Kon-no, K.; Kitahara, A.; El Seoud, O. A. In Nonionic Surfactants; Schick, M. J., Ed.; Marcel Dekker, Inc.: New York, 1987; Chapter 4.
51. Day, M.; Castoro, J. A.; Wilkins, C. L. Anal. Chem. 1995, 67, 1575 and references therein.
52. Pederson, C. J. J. Am. Chem. Soc. 1967, 89, 7017.
53. See for example: (a) Mattern, D. E.; Hercules, D. M. Anal. Chem. 1985, 57, 2041.
54. (b) Bahr, U.; Deppe, A.; Karas, M.; Hillenkamp, F.; Giessmann, U. Anal. Chem. 1992, 64, 2866.
55. (c) Biais, J. C.; Tessier, M.; Bolbach, G.; Remaud, B.; Rozes, L.; Guittard, J.; Brunot, A.; Maréchal, E.; Tabet, J. C. Int. J. Mass Spectrom. Ion Processes 1995, 144, 131.
56. (d) Montaudo, G.; Montaudo, M. S.; Puglisi, C.; Samperi, F. Rapid Commun. Mass Spectrom. 1995, 9, 453.
57. (e) Thomson, B.; Suddaby, K.; Rudin, A.; Lajoie, G. Eur. Polym. J. 1996, 32, 239.
58. Fendler, J. H. Acc. Chem. Res. 1976, 9, 153.
59. 2Ar), 7.00 (m, 3 aromatic H).
60. (a) Chu, B.; Wu, G. Macromol. Symp. 1995, 90, 251.
61. (b) Robeiro, A. In Reverse Micelles; Luisi, P. L., Straub, B. E., Eds.; Plenum Press: New York, 1984; pp 113-120.
62. Winsor, P. A. Solvent Properties of Amphiphilic Compounds; Butterworths Scientific Publications: London, 1954; Chapter 6.
63. Penfold, J.; Staples, E.; Tucker, I.; Cummins, P. J. Colloid Interface Sci. 1997, 185, 424; and references therein.
64. (a) Harrison, I. T.; Harrison, S. J. Am. Chem. Soc. 1967, 89, 5723.
65. (b) Harrison, I. T. J. Chem. Soc., Chem. Commun. 1972, 231.
66. (a) Harrison, I. T. J. Chem. Soc., Perkin Trans, 1 1974, 301.
67. (b) Harrison, I. T. J. Chem. Soc., Chem. Commun. 1977, 384.
68. Marshall, J. A.; Andersen, N. H.; Schlicher, J. W. J. Org. Chem. 1970, 35, 858.
69. Gibson, H. W.; Lee, S.-H.; Engen, P. T.; Lecavalier, P.; Sze, J.; Shen, Y. X.; Bheda, M. J. Org. Chem. 1993, 58, 3749.
70. See, for example: March, J. Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience: New York, 1985; p 784.
71. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
72. See, for example: Odian, G. Principles of Polymerization, 3rd ed.; Wiley-Interscience: New York, 1991.
73. See, for example: (a) Rasmussen, J. K.; Heilmann, S. M.; Krepski, L. R. In Encyclopedia of Polymer Science and Engineering, 2nd ed.; Mark, H. F., Bikales, N., Overberger, C. G., Menges, G., Eds.; Wiley-Interscience: New York, 1988; Vol. 11, p 558 and references therein, (b) Taylor, L. D.; Kolesinski, H. S.; Mehta, A. C.; Locatell, L.; Larson, P.S. Makromol. Chem., Rapid Commun. 1982, 3, 779. (c) Heilmann, S. M.; Rasmussen, J. K.; Palensky, F. J.; Smith, H. K., II. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 1179.
74. See, for example: (a) Rasmussen, J. K.; Heilmann, S. M.; Krepski, L. R. In Encyclopedia of Polymer Science and Engineering, 2nd ed.; Mark, H. F., Bikales, N., Overberger, C. G., Menges, G., Eds.; Wiley-Interscience: New York, 1988; Vol. 11, p 558 and references therein, (b) Taylor, L. D.; Kolesinski, H. S.; Mehta, A. C.; Locatell, L.; Larson, P.S. Makromol. Chem., Rapid Commun. 1982, 3, 779. (c) Heilmann, S. M.; Rasmussen, J. K.; Palensky, F. J.; Smith, H. K., II. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 1179.
75. See, for example: (a) Rasmussen, J. K.; Heilmann, S. M.; Krepski, L. R. In Encyclopedia of Polymer Science and Engineering, 2nd ed.; Mark, H. F., Bikales, N., Overberger, C. G., Menges, G., Eds.; Wiley-Interscience: New York, 1988; Vol. 11, p 558 and references therein, (b) Taylor, L. D.; Kolesinski, H. S.; Mehta, A. C.; Locatell, L.; Larson, P.S. Makromol. Chem., Rapid Commun. 1982, 3, 779. (c) Heilmann, S. M.; Rasmussen, J. K.; Palensky, F. J.; Smith, H. K., II. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 1179.
76. Drtina, G. J.; Heilmann, S. M.; Moren, D. M.; Rasmussen, J. K.; Krepski, L. R.; Smith, H. K., II; Pranis, R. A.; Turek, T. C. Macromolecules 1996, 29, 4486 and references therein.
77. Campana Filho, S. P.; Goissis, G. J. Chromatogr. 1982, 236, 197.
78. Castoro, J. A.; Köster, C.; Wilkins, C. L. Rapid Commun. Mass Spectrom. 1992, 6, 239.
79. Yao, J.; Dey, M.; Pastor, S. J.; Wilkins, C. L. Anal. Chem. 1995, 67, 3638.
80. Pastor, S. J.; Wilkins, C. L. J. Am. Soc. Mass Spectrom. 1997, 8, 225.
81. Castoro, J. A.; Wilkins, C. L. Anal. Chem. 1993, 65, 2621.