Self-assembly of an amphiphilic [2]rotaxane incorporating a tetrathiafulvalene unit

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3547-3550

  Jeppesen, Jan Oskar ^a,b   Perkins, Julie ^a   Becher, Jan ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001010648     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006387s     Document Type: Article

References (46)

1. (a) Fyfe, M. C. T., Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
2. (b) Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930-944.
3. (c) Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P., Dietrich-Buchecker, C. O., Eds.; VCH-Wiley: Weinheim, 1999.
4. (d) Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643-1663.
5. For a [2]catenane-based solid-state electronically reconfigurable switch, see: (a) Asakawa, M.; Higuchi, M.; Mattersteig, G.; Nakamura, T.; Pease, A. R.; Raymo, F. M.; Shimizu, T.; Stoddart, J. F. Adv. Mater. 2000, 12, 1099-1102.
6. (b) Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172-1175.
7. For electronically configurable molecular-based logic gates, see: (a) Collier, C. P.; Wong, E. W., Belohradsky, M.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 1999, 285, 391-394.
8. (b) Wong, E. W.; Collier, C. P.; Belohradsky, M.; Raymo, F. M. Stoddart, J. F.; Heath, J. R. J. Am. Chem. Soc. 2000, 122, 5831-5840.
9. For TTF reviews, see: (a) Adam, M.; Müllen, K. Adv. Mater. 1994, 6, 439-459.
10. (b) Jørgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 23, 41-51.
11. (c) Bryce, M. R. J. Mater. Chem. 1995, 5, 1481-1496.
12. (d) Garin, J. Adv. Heterocycl. Chem. 1995, 62, 249-304.
13. (e) Schukat, G.; Fanghänel, E. Sulfur Rep. 1996, 18, 1-294.
14. (f) Bryce, M. R. J. Mater. Chem. 2000, 10, 589-598.
15. (g) Nielsen, M. B.; Lomholdt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153-164.
16. (a) Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 1584-1586.
17. (b) Asakawa, M.; Dehaen, W.; L'abbé, G.; Menzer, S.; Nouwen, J.; Raymo, F. M.; Stoddart J. F.; Williams, D. J. J. Org. Chem. 1996, 51, 9591-9595.
18. For examples of catenanes, rotaxanes and pseudorotaxanes containing TTF, see: (a) Ashton, P. R.; Bissell, R. A.; Spencer, N.; Stoddart, J. F.; Tolley, M. S. Synlett 1992, 923-926.
19. (b) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342.
20. (c) Li, Z.-T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528.
21. (d) Li, Z.-T.; Becher, J. Chem. Commun. 1996, 639-640.
22. (e) Li, Z.-T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633.
23. (f) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Montalti, N.; Spencer, N.; Stoddart, J. F.; Venturi, M. Chem. Eur. J. 1997, 3, 1992-1996.
24. (f) Li, Z.-T.; Becher, J. Synlett 1997, 557-560.
25. (g) Nielsen, M. B.; Li, Z.-T.; Becher. J. J. Mater. Chem. 1997, 7, 1175-1187.
26. (h) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Hamers, C.; Mattersteig, G.; Montalti, N.; Shipway, A. N.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Venturi, M.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 1998, 37, 333-337.
27. (i) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans, 1 1998, 1305-1308.
28. (j) Credi, A.; Montalti, M.; Balzani, V.; Langford, S. J.; Raymo, F. M.; Stoddart, J. F. New J. Chem. 1998, 22, 1061-1065.
29. (k) Asakawa, M.; Ashton, P. R.; Balzani, V.; Boyd, S. E.; Credi, A.; Mattersteig, G.; Menzer, S.; Montalti, M.; Raymo, F. M.; Ruffilli, C.; Stoddart, J. F.; Venturi, M.; Williams, D. J. Eur. J. Org. Chem. 1999, 985-994.
30. (l) Lau, J.; Nielsen, M. B.; Thorup, N.; Cava, M. P.; Becher, J. Eur. J. Org. Chem. 1999, 3335-3341.
31. (m) Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Raymo, F. M.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 1924-1936.
32. (n) Damgaard, D.; Nielsen, M. B.; Lau, J.; Jensen, K, B.; Zubarev, R.; Levillian, E.; Becher, J. J. Mater. Chem. 2000, 10, 2249-2258.
33. Recently, two of us developed an efficient synthesis of the pyrrolo-[3,4-d]tetrathiafulvalene ring system using a simple and nonclassical pyrrole synthesis. See: (a) Jeppesen, J. O.; Takimiya, K.; Jensen, F.; Becher, J. Org. Lett. 1999, 1, 1291-1294.
34. (b) Jeppesen, J. O.; Takimiya, K.; Jensen, F.; Brimert K.; Nielsen, K.; Thorup, N.; Becher J. J. Org. Chem. 2000, 65, 5794-5805.
35. Simonsen, K. B.; Svenstrup, N.; Lau, J.; Simonsen, O.; Mørk, P.; Kristensen, G. J.; Becher. J. Synthesis 1996, 407-418.
36. Although the synthesis of 3 has been described before in the literature (see ref 7b), it was prepared by a different route and only on a very small scale.
37. Ashton, P. R.; Ballardini, R.; Balzani, V.; Belohradsky, 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.
38. Although we have previously used (see ref 10) compound 4 as its potassium salt in alkylations, we now prefer to isolate it directly as the phenol after an acid-catalyzed reaction between bis(4-tert-butytphenyl)-4-ethylphenylmethanol and pnenol, followed by silica gel column chromatography and recrystallization from hexane.
39. Gibson, H. W.; Lee, S.-H.; Engen, P. T.; Lecavalier, P.; Sze, J.; Shen, Y. X.; Bheda, M. J. Org. Chem. 1993, 58, 3748-3756.
40. Percec, V.; Cho. W.-D.; Mosier, P. E.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 1998, 120, 11061-11070 and references therein.
41. Satoru, I.; Hideo, M.; Kiyoshi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1357-1360.
42. 6 (1737.3): C, 67.75; H, 6.56; N, 0.81. Found: C, 67.61; H. 6.46; N, 0.80.
43. 2O (2837.6): C, 56.00; H, 5.23; N, 2.44. Found: C, 56.07; H, 5.06; N, 2.28.
44. Unreacted dumbbell can be recovered and reused.
45. 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.
46. Devonport, W.; Blower, M. A.; Bruce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887.