The slipping approach to self-assembling [n]rotaxanes

Journal of the American Chemical Society

Volumn 119, Issue 2, 1997, Pages 302-310

  Asakawa, Masumi ^a   Ashton, Peter R ^a   Ballardini, Roberto ^b   Balzani, Vincenzo ^c   Bělohradský, Martin ^a   Gandolfi, Maria Teresa ^c   Kocian, Oldrich ^a   Prodi, Luca ^c   Raymo, Françisco M ^a   Stoddart, J Fraser ^a   Venturi, Margherita ^c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b Istituto di Fotochimica e Radiazioni d'Alta Energia   (Italy)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE; SPECTROPHOTOMETRY;

EID: 0031041828     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961817o     Document Type: Article

References (31)

1. (a) Whitesides, G. M.; Simanek, E. R.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
2. (b) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260.
3. (c) Raymo, F. M.; Stoddart, J. F. Curr. Op. Coll. Interf. Sci. 1996, 1, 116-126.
4. (d) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
5. (a) Gibson, H. W.; Bheda, M. C.; Engen, P. T. Prog. Polym. Sci. 1994, 19, 843-945.
6. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
7. (c) Bělohradský, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43.
8. (a) Ashton, P. R.; Bělohradský, M.; Philp, D.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1993, 1269-1274.
9. (b) Ashton, P. R.; Bělohradský, M.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1993, 1274-1277.
10. (c) Amabilino, D. B.; Ashton, P. R.; Bělohradský, M.; Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 751-753.
11. (d) Bělohradský, M.; Philp, D.; Raymo, F. M.; Stoddart, J. F. In Organic Reactivity: Physical and Biological Aspects; Golding, B. T., Griffin, R. J., Maskill, H., Eds.; RSC Special Publication No. 148: Cambridge, 1995; pp 387-398.
12. (e) Ashton, P. R.; Ballardini, R.; Balzani, V.; Bělohradský, M.; Gandolfi, M. T.; Philp, D.; Prodi, L.; Raymo, F. M.; Reddington, M. V.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 4931-4951.
13. 2 (Figure 2), respectively. The compounds methoxybenzene, 1,4-dimethoxybenzene, 1,5-dimethoxynaphthalene, and 2,7-dimethoxynaphthalene are abbreviated to MB, 1/4DMB, 1/5DMN, and 2/7DMN (Figures 4 and 5), respectively. The acronyms employed to indicate the dumbbell-shaped compounds depicted in Scheme 1 and Figure 3 are composed of the common alphabetical notation corresponding to the R groups attached to the stoppers followed by the letter D which stands for dumbbell. The bis(tert-butylphenyl)-4-isopropylphenylmethane-based chloride shown in Scheme 3 and the tetraarylmethane-based model compound shown in Figure 5 are abbreviated to i-Pr-S and R-S where S stands for stopper. The acronyms, corresponding to the macrocyclic polyethers depicted in Figure 2, indicate the nature of the two aromatic units incorporated into each macrocycle. Thus, HQ, 1/5DN, and 2/7DN stand for hydroquinone, 1,5-dioxynaphthalene, 2,7-dioxynaphthalene, and so on. Numbers are employed for the remaining compounds.
14. Amabilino, D. B.; Ashton, P. R.; Bělohradský, M.; Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 747-750.
15. -1 at 215 K for the degenerate site-exchange process - namely, the shuttling of the macrocyclic component from one bipyridinium recognition site to the other - occurring within [2]rotaxanes incorporating either tris(4-tert-butylPhenylmethyl groups (R = t-Bu) or phenylbis(4-tert-butylpheny)methyl groups (R = H) as the stoppers was derived by the coalescence method. See refs 3b,e and: Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1992, 1124-1128.
16. (a) Allwood, B. L.; Spencer, N.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1064-1066.
17. (b) Ashton, P. R.; Chrystal, E. J. T.; Mathias, J. P.; Parry, K. P.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Tetrahedron Lett. 1987, 28, 6367-6370.
18. (c) Ortholand, J. Y.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1394-1397.
19. (d) Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
20. (e) Asakawa, M.; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. J. Org. Chem. In press.
21. Equation 1 was determined as reported in the Supporting Information. For further information, see: Laidler, K. J. Chemical Kinetics; Harper Collins Publisher: New York, 1987.
22. e and the molar extinction coefficient ∈ of one of the [2]rotaxanes shown in Scheme 1 or the [2]rotaxane 1, respectively, under the same conditions of the experiment. The value of ∈ is not affected by the nature of the R groups linked to the tetraarylmethane-based stoppers. See ref 3e.
23. Riddick, J. A.; Bunger, W. B. Organic Solvents, Techniques of Chemistry; Wiley: New York, 1970; Vol. 2.
24. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988.
25. (a) Kosower, E. M. J. Am. Chem. Soc. 1958, 80, 3253-3260.
26. (b) Kosower, E. M. J. Am. Chem. Soc. 1958, 80, 3261-3267.
27. Kosower, E. M. J. Am. Chem. Soc. 1958, 80, 3267-3270.
28. Richardson, D. E.; Taube, H. Inorg. Chem. 1981, 20, 1278-1285.
29. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G. A.; Tatchell, R. Practical Organic Chemistry, Longman: New York, 1989.
30. Berlman, Handbook of Fluorescence Spectra of Aromatic Compounds, Academic Press: London, 1965.
31. Armaroli, N.; Balzani, V.; Barigelletti, F.; De Cola, L.; Flamigni, L.; Sauvage, J.-P.; Hemmert, C. J. Am. Chem. Soc. 1994, 116, 5211-5217.