Catenane formation from two molecular rings through very rapid slippage. A möbius strip mechanism

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 899-900

  Fujita, Makoto ^a   Ibukuro, Fumiaki ^a   Seki, Hiroko ^a   Karno, Osamu ^b   Imanari, Mamoru ^b   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

^b JEOL LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000955402     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9507325     Document Type: Article

References (34)

1. Fujita, M., Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720.
2. For reviews, see the following: (a) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J.-C. In Comprehensive Supra-molecular Chemistry; Lehn, J.-M. Ed.; Pergamon Press: Oxford, 1996; Chapter 2 (in press). (b) Stoddart, J. F., Raymo, F.; Amabilino, D. B. In Comprehensive Supra-molecular Chemistry; Lehn, J.-M. Ed.; Pergamon Press: Oxford, 1996; Chapter 3 (in press).
3. For reviews, see the following: (a) Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Chambron, J.-C. In Comprehensive Supra-molecular Chemistry; Lehn, J.-M. Ed.; Pergamon Press: Oxford, 1996; Chapter 2 (in press). (b) Stoddart, J. F., Raymo, F.; Amabilino, D. B. In Comprehensive Supra-molecular Chemistry; Lehn, J.-M. Ed.; Pergamon Press: Oxford, 1996; Chapter 3 (in press).
4. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
5. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
6. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
7. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
8. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
9. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
10. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
11. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
12. For recent other catenane syntheses, see the following: (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303. (b) Vögtle, F.; Meier, S.; Hoss, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1619. (c) O.-Hildebrandt, S.; Meier, S.; Schmidt, W.; Vögtle, F. Angew. Chem , Int. Ed. Engl. 1994, 33, 1767. (d) Gunter, M. J.; Hockless, D. C. R.; Johnston, M. R.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 1994, 116, 4810. (e) Gruter, G.-J.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179. (f) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582. (g) Johnston, A. G.; Leigh, D. A., Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (h) Johnston, A. G., Leigh, D. A.; Nezhat, L., Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212. (i) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894.
13. Ligand exchange on Pd(II) is a very rapid process: Basolo, F.; Chatt, J.; Gray, H. B.; Pearson, R. G., Shaw, B. L. J. Chem. Soc. 1961, 2207.
14. (a) Noggle, J. H., Schirmer, R. E. The Nuclear Overhauser Effect: Academic Press: New, York, 1971.
15. (b) Dahlquist, F. W., Longmuir, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406.
16. (c) Wagner, G.; Wuthrich, K. J Magn. Reson. 1979, 33, 675.
17. Compare with a very slow rotaxane self-assembly involving complete dissociation of a Fe(III) - py coordinate bond: Wylie, S.; Macartney, D. H. J. Am. Chem. Soc. 1992, 114, 3136.
18. 4 (outside), though only one form is shown in eq 2.
19. (a) Fujita, M., Ibukuro, F.; Yamaguchi, Y.; Ogura, K. J Am. Chem. Soc. 1995, 117, 4175.
20. 8a showed that this molecule was very tight and the internal rotation was impossible.
21. Fujita, M.; Yazaki, J.; Ogura, K. Chem. Lett. 1991, 1031.
22. Species 2* stands for 2 in which a phenylene ring is magnetically saturated.
23. This stage is an unsteady state because the increase of signal intensities of 2* and 1** is not saturated yet.
24. If no intermediate existed, 1** had to be formed directly from 1* or consecutively via 2*. However, both paths were negated by the NMR study, as discussed.
25. Internal rotation of one ring during a momentary dissociation of another ring could explain the NMR results. However, this process does not meet the scrambling experiments using 4 discussed later.
26. 4 of 2 varied as follows: δ 7.07, 7.00, 6.86, and 6.69 at 1, 10, 25, and 50 mM/Pd, respectively. Original spectra were provided in Figure 1B of ref 1.
27. Fujita, M.; Nagao, S.; Iida, M.; Ogata, K.; Ogura, K. J. Am. Chem. Soc. 1993, 115, 1574.
28. 16
29. -1 by an MM2 study, where MM2 parameters supplied by the CAChe system (Ver 3.5. Sony/Tektronix Corp.) were used for the refinement of the molecular modeling (see Supporting Information).
30. van Gulick, N New J. Chem. 1993, 17, 619. A preprint of this paper was first written in 1960: see the preface to this paper by Walba: New J. Chem. 1993, 17, 618.
31. van Gulick, N New J. Chem. 1993, 17, 619. A preprint of this paper was first written in 1960: see the preface to this paper by Walba: New J. Chem. 1993, 17, 618.
32. Strictly speaking, a Mobius strip, when cut in half, always gives one piece like intermediate A, a strip that leads to the catenane upon cutting of the strip is not a Möbius strip. However, the overgeneralization regarding twisted strips seems to be accepted in older literature, and we hope one can easily understand what is meant by our "Mobius strip mechanism", although it does not involve a real Möbius strip.
33. Walba, D. M.; Richards, R. M.; Haltiwanger, R. C. J Am. Chem. Soc. 1982, 104, 3219. Walba, D. M.; Homan, T. C.; Richards, R. M ; Haltiwanger, R. C. New J. Chem. 1993, 17, 661.
34. Walba, D. M.; Richards, R. M.; Haltiwanger, R. C. J Am. Chem. Soc. 1982, 104, 3219. Walba, D. M.; Homan, T. C.; Richards, R. M ; Haltiwanger, R. C. New J. Chem. 1993, 17, 661.