Relative threading efficiencies of different macrocycles: A competitive trapping methodology based on hybrid polyrotaxanes

Macromolecules

Volumn 30, Issue 26, 1997, Pages 8524-8525

  Gong, Caiguo ^a   Gibson, Harry W ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION REACTIONS; CROWN ETHERS; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; POLYCONDENSATION; SYNTHESIS (CHEMICAL);

ASSOCIATION CONSTANTS; CAPTURE CONSTANTS; POLYROTAXANE; THREADING EFFICIENCY;

AROMATIC POLYMERS;

EID: 0031332167     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9711405     Document Type: Article

References (32)

1. (a) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843.
2. (b) Amabilino, D. B.; Stoddart, J. F. chem. Rev. 1995, 95, 2725.
3. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
4. (d) Gibson, H. W. In Large Ring Molecules, Semlyen, J. A., Ed.; J. Wiley and Sons: New York, 1996; pp 191-262.
5. (a) Wenz, G. Macromol. Symp. 1994, 87, 11.
6. (b) Weickenmeier, M.; Wenz, G. Macromol. Rapid. Commun. 1996, 17, 731.
7. (c) Steinbrunn, M. B.; Wenz, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2139.
8. (d) Herrmann, W.; Keller, B.; Wenz, G. Macromolecules 1997, 30, 4966.
9. (a) Born, M.; Ritter, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 309.
10. (b) Born, M.; Ritter, H. Adv. Mater. 1996, 8, 149.
11. (c) Born, M.; Ritter, H. Macromol. Rapid Commun. 1996, 17, 197.
12. (a) Harada, A.; Li, J.; Kamachi, M. Macromolecules 1994, 27, 4538.
13. (b) Harada, A.; Okada, M.; Li, J.; Kamachi, M. Macromolecules 1995, 28, 8406.
14. (a) Shen, Y. X.; Xie, D.; Gibson, H. W. J. Am. Chem. Soc. 1994, 116, 537.
15. (b) Gibson, H. W.; Liu, S.; Lecavalier, P.; Wu, C.; Shen, Y. X. J. Am. Chem. Soc. 1995, 117, 852.
16. (c) Gibson, H. W.; Liu, S.; Gong, C.; Ji, Q.; Joseph, E. Macromolecules 1997, 30, 3711.
17. (e) Gibson, H. W.; Liu, S. Macromol. Symp. 1996, 102, 55.
18. (f) Gong, C.; Gibson, H. W. Angew. Chem. Int. Ed. Engl. 1997, 36, 2331.
19. (a) Gong, C.; Gibson, H. W. Macromolecules 1996, 29, 7029.
20. (b) Gong, C.; Gibson, H. W. Macromol. Chem. Phys. 1997, 198, 2321.
21. (c) Gong, C.; Ji, Q.; Glass, T. E.; Gibson, H. W. Macromolecules 1997, 30, 4087.
22. (a) Gong, C.; Gibson, H. W. J. Am. Chem. Soc. 1997, 119, 5862.
23. (b) Gong, C.; Gibson, H. W. J. Am. Chem. Soc. 1997, 119, 8585.
24. Gong, C.; Gibson, H. W. Angew. Chem., Int. Ed. Engl., in press.
25. Mason, P. E.; Parsons, I. W.; Tolley, M. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2238.
26. Owen, J.; Hodge, P. J. Chem. Soc., Chem. Commun. 1997, 11.
27. We define a polyrotaxane threaded with two or more different macrocycles as a hybrid polyrotaxane to distinguish it from a polyrotaxane threaded with one type of cyclic.
28. 2- signal at 4.25 ppm (Figure 1b) because these signals are well separated from each other. Substraction of that for proton d (calculated from the integral of proton a) from the total integral for 30C10 and proton d gave the m/n value of 30C10 (estimated relative error for m/n: ± 5%).
29. w = 54K, 36K, and 42K for 5, 6, and 7, respectively (PDI ~ 2.5) by GPC with PS standards.
30. Out of phase rotation of the phenylene rings of BPP34C10 places proton a of one ring in the shielding zone of the other ring. In the polyrotaxane not only is rotation prevented but also the space between the rings is occupied and the aromatic proton a appears at nearly the same chemical shift (6.83 ppm) (Figure 1b) as those in p-dimethoxybenzene (6.85 ppm).
31. DB24C8 has produced low molecular mass pesudorotaxanes: (a) Ashton, P. R.; Campbell, P. J.; Chrystal, E. S. T.; Glink, P. J.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865. (b) Ashton, P. R.; Chrystal, E. S. T.; Glink, P. J.; Menzer, S.; Shiavo, C.; Spencer, N.; Stoddart, J. F.; Tasker, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1869.
32. DB24C8 has produced low molecular mass pesudorotaxanes: (a) Ashton, P. R.; Campbell, P. J.; Chrystal, E. S. T.; Glink, P. J.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865. (b) Ashton, P. R.; Chrystal, E. S. T.; Glink, P. J.; Menzer, S.; Shiavo, C.; Spencer, N.; Stoddart, J. F.; Tasker, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1869.