SCOPUS 정보 검색 플랫폼

Macromolecules

Volumn 32, Issue 5, 1999, Pages 1559-1569

Threading/Dethreading Exchange Rates as Structural Probes in Polypseudorotaxanes

(3) Mason, Philip E a Bryant, William S a Gibson, Harry W a

a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; GLYCEROL; MACROMOLECULES; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYURETHANES; SYNTHESIS (CHEMICAL);

POLYPSEUDOROTAXANES;

AROMATIC POLYMERS;

EID: 0033537559 PISSN: 00249297 EISSN: None Source Type: Journal
DOI: 10.1021/ma9807769 Document Type: Article

Times cited : (59)

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- For early reports on rotaxanes, see: (a) Harrison, I. T.; Harrison, S. J. Am. Chem. Soc. 1967, 89, 5723. Schill, G.; Zollenkopf, H. Nachr. Chem. Tech. 1967, 79, 149. (b) Harrison, I. T. J. Chem. Soc., Perkin Trans. 1 1974, 301. (c) Schill, G.; Beckmann, W.; Schweickert, N.; Fritz, H. Chem. Ber. 1986, 119, 2647. More recent papers, see: (d) Wu, C.; Lecavalier, P. R.; Shen, Y. X.; Gibson, H. W. Chem. Mater. 1991, 3, 570. (e) Schenning, A. P. H. J.; de Bruin, B.; Rowan, A. E.; Kooijman, H.; Spek, A. L.; Nolte, R. J. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2132. (f) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashiraa, N. J. Am. Chem. Soc. 1997, 119, 7605. (g) Anderson, S.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 13130. Anderson, S.; Clegg, W.; Anderson, H. L. J. Chem. Soc., Chem. Commun. 1998, 2379. (h) Dünnwald, T.; Jäger, R.; Vögtle, F. Chem. Eur. J. 1998, 4, 2043. (i) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092. (j) Gavina, P.; Sauvage, J.-P. Tetrahedron Lett. 1997, 38, 3521. (k) Rowan, A. E.; Aarts, P. P. M.; Koutstaal, K. W. M. J. Chem. Soc., Chem. Commun. 1998, 611. (l) Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297. Raymo, F. M.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 1998, 120, 9318.
- (1997) Tetrahedron Lett. , vol.38 , pp. 3521
- Gavina, P.¹ Sauvage, J.-P.²

13
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- For early reports on rotaxanes, see: (a) Harrison, I. T.; Harrison, S. J. Am. Chem. Soc. 1967, 89, 5723. Schill, G.; Zollenkopf, H. Nachr. Chem. Tech. 1967, 79, 149. (b) Harrison, I. T. J. Chem. Soc., Perkin Trans. 1 1974, 301. (c) Schill, G.; Beckmann, W.; Schweickert, N.; Fritz, H. Chem. Ber. 1986, 119, 2647. More recent papers, see: (d) Wu, C.; Lecavalier, P. R.; Shen, Y. X.; Gibson, H. W. Chem. Mater. 1991, 3, 570. (e) Schenning, A. P. H. J.; de Bruin, B.; Rowan, A. E.; Kooijman, H.; Spek, A. L.; Nolte, R. J. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2132. (f) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashiraa, N. J. Am. Chem. Soc. 1997, 119, 7605. (g) Anderson, S.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 13130. Anderson, S.; Clegg, W.; Anderson, H. L. J. Chem. Soc., Chem. Commun. 1998, 2379. (h) Dünnwald, T.; Jäger, R.; Vögtle, F. Chem. Eur. J. 1998, 4, 2043. (i) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092. (j) Gavina, P.; Sauvage, J.-P. Tetrahedron Lett. 1997, 38, 3521. (k) Rowan, A. E.; Aarts, P. P. M.; Koutstaal, K. W. M. J. Chem. Soc., Chem. Commun. 1998, 611. (l) Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297. Raymo, F. M.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 1998, 120, 9318.
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- Rowan, A.E.¹ Aarts, P.P.M.² Koutstaal, K.W.M.³

14
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- For early reports on rotaxanes, see: (a) Harrison, I. T.; Harrison, S. J. Am. Chem. Soc. 1967, 89, 5723. Schill, G.; Zollenkopf, H. Nachr. Chem. Tech. 1967, 79, 149. (b) Harrison, I. T. J. Chem. Soc., Perkin Trans. 1 1974, 301. (c) Schill, G.; Beckmann, W.; Schweickert, N.; Fritz, H. Chem. Ber. 1986, 119, 2647. More recent papers, see: (d) Wu, C.; Lecavalier, P. R.; Shen, Y. X.; Gibson, H. W. Chem. Mater. 1991, 3, 570. (e) Schenning, A. P. H. J.; de Bruin, B.; Rowan, A. E.; Kooijman, H.; Spek, A. L.; Nolte, R. J. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2132. (f) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashiraa, N. J. Am. Chem. Soc. 1997, 119, 7605. (g) Anderson, S.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 13130. Anderson, S.; Clegg, W.; Anderson, H. L. J. Chem. Soc., Chem. Commun. 1998, 2379. (h) Dünnwald, T.; Jäger, R.; Vögtle, F. Chem. Eur. J. 1998, 4, 2043. (i) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092. (j) Gavina, P.; Sauvage, J.-P. Tetrahedron Lett. 1997, 38, 3521. (k) Rowan, A. E.; Aarts, P. P. M.; Koutstaal, K. W. M. J. Chem. Soc., Chem. Commun. 1998, 611. (l) Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297. Raymo, F. M.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 1998, 120, 9318.
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- Ashton, P.R.¹ Baxter, I.² Fyfe, M.C.T.³ Raymo, F.M.⁴ Spencer, N.⁵ Stoddart, J.F.⁶ White, A.J.P.⁷ Williams, D.J.⁸

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- For early reports on rotaxanes, see: (a) Harrison, I. T.; Harrison, S. J. Am. Chem. Soc. 1967, 89, 5723. Schill, G.; Zollenkopf, H. Nachr. Chem. Tech. 1967, 79, 149. (b) Harrison, I. T. J. Chem. Soc., Perkin Trans. 1 1974, 301. (c) Schill, G.; Beckmann, W.; Schweickert, N.; Fritz, H. Chem. Ber. 1986, 119, 2647. More recent papers, see: (d) Wu, C.; Lecavalier, P. R.; Shen, Y. X.; Gibson, H. W. Chem. Mater. 1991, 3, 570. (e) Schenning, A. P. H. J.; de Bruin, B.; Rowan, A. E.; Kooijman, H.; Spek, A. L.; Nolte, R. J. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2132. (f) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashiraa, N. J. Am. Chem. Soc. 1997, 119, 7605. (g) Anderson, S.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 13130. Anderson, S.; Clegg, W.; Anderson, H. L. J. Chem. Soc., Chem. Commun. 1998, 2379. (h) Dünnwald, T.; Jäger, R.; Vögtle, F. Chem. Eur. J. 1998, 4, 2043. (i) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092. (j) Gavina, P.; Sauvage, J.-P. Tetrahedron Lett. 1997, 38, 3521. (k) Rowan, A. E.; Aarts, P. P. M.; Koutstaal, K. W. M. J. Chem. Soc., Chem. Commun. 1998, 611. (l) Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297. Raymo, F. M.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 1998, 120, 9318.
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- Raymo, F.M.¹ Houk, K.N.² Stoddart, J.F.³

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- For reviews of rotaxanes, catenanes, and polyrotaxanes see: (a) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Engl. 1996, 35, 1154. (d) Gibson, H. W. In Large Ring Molecules; Semlyen, A. J., Ed.; J. Wiley and Sons: New York, 1996; pp 191-262. (e) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (f) Gong, C.; Gibson, H. W. Curr. Opin. Solid State Mater. Sci. 1998, 2, 647. (f) Nepolgodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1959.
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- Gibson, H.W.¹ Bheda, M.C.² Engen, P.T.³

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- For reviews of rotaxanes, catenanes, and polyrotaxanes see: (a) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Engl. 1996, 35, 1154. (d) Gibson, H. W. In Large Ring Molecules; Semlyen, A. J., Ed.; J. Wiley and Sons: New York, 1996; pp 191-262. (e) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 931. (f) Gong, C.; Gibson, H. W. Curr. Opin. Solid State Mater. Sci. 1998, 2, 647. (f) Nepolgodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1959.
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- Gunter, M.J.¹ Hockless, D.C.R.² Johnston, M.R.³ Skelton, B.W.⁴ White, A.H.⁵

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- Catenanes: (a) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (b) Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. (c) Amaroli, N.; Diederich, F.; Dietrich-Buchecker, C. O.; Flamigni, L.; Marconi, G.; Nierengarten, J.-F.; Sauvage, J.-P. Chem. Eur. J. 1998, 4, 406. (d) Amabilino, D. B.; Ashton, P. R.; Boyd, S. E.; Lee, J. Y.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2070. (e) Muscat, D.; Witte, A.; Köhler, W.; Müllen, K.; Geerts, Y. Macromol. Rapid Commun. 1997, 18, 233. (f) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608. (g) Amabilino, D. B.; Ashton, P. R.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1998, 4, 460. Hamers, C.; Raymo, F. M.; Stoddart, J. F. Eur. J. Org. Chem. 1998, 2109.
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- Adams, H.¹ Carver, F.J.² Hunter, C.A.³

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- Amaroli, N.¹ Diederich, F.² Dietrich-Buchecker, C.O.³ Flamigni, L.⁴ Marconi, G.⁵ Nierengarten, J.-F.⁶ Sauvage, J.-P.⁷

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- Catenanes: (a) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (b) Adams, H.; Carver, F. J.; Hunter, C. A. J. Chem. Soc., Chem. Commun. 1995, 809. (c) Amaroli, N.; Diederich, F.; Dietrich-Buchecker, C. O.; Flamigni, L.; Marconi, G.; Nierengarten, J.-F.; Sauvage, J.-P. Chem. Eur. J. 1998, 4, 406. (d) Amabilino, D. B.; Ashton, P. R.; Boyd, S. E.; Lee, J. Y.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2070. (e) Muscat, D.; Witte, A.; Köhler, W.; Müllen, K.; Geerts, Y. Macromol. Rapid Commun. 1997, 18, 233. (f) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608. (g) Amabilino, D. B.; Ashton, P. R.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1998, 4, 460. Hamers, C.; Raymo, F. M.; Stoddart, J. F. Eur. J. Org. Chem. 1998, 2109.
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- 8c

74
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- 8c

75
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76
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- bound is taken as equal to the chemical shift of the type 1 peak.

77
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- -1. Thus, the kinetics of the present system are considerably slower, as expected and indeed desired for a slippage system.

80
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- -1 was required, making this treatment no better than the simple analysis given in the text. The ABAKUS treatment could not be confidently used for 13-15 for two reasons: (1) again K is not known, and (2) the number and type of binding sites between BPA units vary. The latter problem is significant because ABAKUS was designed for a system with only a single guest site between blocking groups and assumes that a cyclic must hop to the next inward site before another ring can thread; with the copolymers 13-15 this is not required.

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