Templated synthesis of desymmetrized [2]catenanes with excellent translational selectivity

Organic Letters

Volumn 9, Issue 13, 2007, Pages 2577-2580

  Liu, Yi ^a   Klivansky, Liana M ^a   Khan, Saeed I ^b   Zhang, Xiyun ^c  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c R and D Project Development and Management   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547201954     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070970s     Document Type: Article

References (48)

1. (a) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810.
2. (b) Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
3. (a) Schill, G. Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971.
4. (b) Molecular Catenanes, Rotaxanes, and Knots; Sauvage, J.-P., Dietrich-Buchecker, C. O., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
5. (a) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
6. (b) Hamilton, D. G.; Sanders, J. K. M.; Davies, J. E.; Clegg, W.; Teat, S. J. Chem. Commun. 1997, 897-898.
7. (c) Hamilton, D. G.; Feeder, N.; Prodi, L.; Teat, S. J.; Clegg, W.; Sanders, J. K. M. J. Am. Chem. Soc. 1998, 120, 1096-1097.
8. (a) Fujita, M.; Ibukuro, F.; Hagihar, H.; Ogura, K. Nature 1994, 367, 720-723.
9. (b) Dietrich-Buchecker, C. O.; Colasson, B.; Fujita, M.; Hori, A.; Geum, N.; Sakamoto, S.; Yamaguchi, K.; Sauvage, J.-P. J. Am. Chem. Soc. 2003, 125, 5717-5725.
10. (c) Fuller, A.-M.; Leigh, D. A.; Lusby, P. J.; Oswald, I. D. H.; Parsons, S.; Walker, D. B. Angew. Chem., Int. Ed. 2004, 43, 3914-3918.
11. (a) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311.
12. (b) Johnston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209-1212.
13. (c) Vogtle, F.; Dunnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451-460.
14. Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396-1399.
15. (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 112, 3484-3530.
16. (b) Dietrich-Buchecker, C. O.; Jimenez-Molero, M. C.; Sartor, V.; Sauvage, J.-P. Pure Appl. Chem. 2003, 75, 1383-1393.
17. (c) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines - A Journey into the Nano World; Wiley-VCH: Weinheim, Germany, 2003.
18. (d) Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191.
19. (a) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Hamers, C.; Mattersteig, G.; Montalti, M.; 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.
20. (b) Tseng, H.-R.; Vignon, S. A.; Stoddart, J. F. Angew. Chem. Int. Ed. 2003, 43, 1491-1495.
21. (c) Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055-2056.
22. (d) de Jong, J. J. D.; Lucas, L. N.; Kellogg, R. M.; van Esch, J. H.; Feringa, B. L. Science 2004, 304, 278-281.
23. (e) Leigh, D. A.; Morales, M. A. F.; Perez, E. M.; Wong, J. K. Y.; Saiz, C. G.; Slawin, A. M. Z.; Carmichael, A. J.; Haddleton, D. M.; Brouwer, A. M.; Buma, W. J.; Wurpel, G. W. H.; Leon, S.; Zerbetto, F. Angew. Chem., Int. Ed. 2005, 44, 3062-3067.
24. (f) Serreli, V.; Lee, C.-F.; Kay, E. R.; Leigh, D. A. Nature 2007, 445, 523-527.
25. (a) 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.
26. (b) Luo, Y.; Collier, C. P.; Jeppesen, J. O.; Nielsen, K. A.; Delonno, E.; Ho, G.; Perkins, J.; Tseng, H.-R.; Yamamoto, T.; Stoddart, J. F.; Heath, J. R. ChemPhysChem 2002, 3, 519-525.
27. (c) Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. F. Science 2004, 306, 2055-2056.
28. (d) Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; Delonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414-417.
29. (a) Nguyen, T. D.; Tseng, H.-R.; Celestre, P. C.; Flood, A. H.; Liu, Y.; Zink, J. I.; Stoddart, J. F. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10029-10034.
30. (b) Nguyen, T. D.; Liu, Y.; Saha, S.; Leung, K. C.-F.; Stoddart, J. F.; Zink, J. I. J. Am. Chem. Soc. 2007, 129, 626-634.
31. (a) Huang, T. J.; Brough, B.; Ho, C.-M.; Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Vignon, S. A.; Tseng, H.-R.; Stoddart, J. F.; Baller, M.; Magonov, S. Appl. Phys. Lett. 2004, 85, 5391-5393.
32. (b) Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H.-R.; Jeppesen, J. O.; Huang, T. J.; Brough, B.; Baller, M.; Magonov, S.; Solares, S. D.; Goddard, W. A.; Ho, C.-M.; Stoddart, J. F. J. Am. Chem. Soc. 2005, 127, 9745-9759.
33. For examples of desymmetrized [2]catenanes with various degrees of control on translational selectivity, see: (a) Ashton, P. R.; Perez-Garcia, L.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 571-574.
34. (b) Baumann, F.; Livoreil, A.; Kaim, W.; Sauvage, J.-P. Chem. Commun. 1997, 35-36.
35. (c) Balzani, V.; Credi, A.; Langford, S. J.; Raymo, F. M.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 2000, 122, 3542-3543.
36. (d) Tseng, H.-R.; Vignon, S. A.; Celestre, P. C.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 2003, 9, 543-556.
37. (e) Hernandez, J. V.; Kay, E. R.; Leigh, D. A. Science 2004, 306, 1532-1537.
38. (a) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-617.
39. (b) Hamilton, D. G.; Montalti, M.; Prodi, L.; Fontani, M.; Zanello, P.; Sanders, J. K. M. Chem. Eur. J. 2000, 6, 608-617.
40. (c) Hansen, J. G.; Feeder, N.; Hamilton, D. G.; Gunter, M. J.; Becher, J.; Sanders, J. K. M. Org. Lett. 2000, 2, 449-452.
41. (d) Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y.-F.; Bond, A. D.; Sanders, J. K. M. Angew. Chem., Int. Ed. 2004, 43, 1959-1962.
42. (e) Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J. K. M.; Stoddart, J. F. J. Am. Chem. Soc. 2004, 126, 9884-9885.
43. (f) Iijima, T.; Vignon, S. A.; Tseng, H.-R.; Jarrosson, T.; Sanders, J. K. M.; Marchioni, F.; Venturi, M.; Apostoli, E.; Balzani, V.; Stoddart, J. F. Chem. Eur. J. 2004, 10, 6375-6392.
44. Credi, A.; Monalti, M.; Balzani, V.; Langford, S. J.; Raymo, F. M.; Stoddart, J. F. New J. Chem. 1998, 22, 1061-1065.
45. 6 were obtained from a MeCN solution after diffusion of diisopropyl ether. For more cristallographic information, please see the crystallographic information files in the Supporting Information.
46. Multiple [C-H⋯O] interactions are observed between several oxygen atoms in the polyether loops of the crown ether and one α-BPy proton, one p-phenylene proton, and one methylene proton of the dicationic cyclophane. The associated [H⋯O] distances are 2.61, 2.50, and 2.47 Å, respectively. The corresponding [C-H⋯O] angles are 165°, 127°, and 134°. In addition, there is [C-H⋯π] interaction between one of the H-4/8 protons of the "inside" DNP ring system and its proximal p-phenylene ring. The distances between the H atom and the centroid π-electron plane is 2.54 Å, and the corresponding [C-H⋯π] angle is 149°.
47. 6, such activation barrier is difficult to measure on account of the absence of other isomers. However, they should be very similar to those reported systems, both of which involve the breaking of donor-acceptor interactions between BPy and the outer aromatic ring system.
48. The electrostatic potential surfaces were generated with MOE2006, using the MMFF94x force field. MOE2006 is a product of the Chemical Computing Group, Montreal, Canada.