A Mechanically Interlocked Bundle

Chemistry - A European Journal

Volumn 10, Issue 8, 2004, Pages 1926-1935

  Badjić, Jovica D ^a   Balzani, Vincenzo ^b   Credi, Alberto ^b   Lowe, James N ^a   Silvi, Serena ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Hydrogen bonds; Luminescence; Molecular recognition; Multivalency; Self assembly

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; CHEMICAL BONDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CYCLOADDITIONS; MOLECULAR BUNDLE; MOLECULAR MACHINE;

ETHERS;

ACETONITRILE; AMMONIUM DERIVATIVE; DICHLOROMETHANE; METHYL CHLORIDE;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; COVALENT BOND; CYCLOADDITION; LUMINESCENCE; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 2342488763     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305687     Document Type: Article

References (131)

1. For some recent examples, see: a) C.-Y. Su, Y.-P. Cai, C.-L. Chen, F. Lissner, B.-S. Kang, W. Kaim, Angew. Chem. 2002, 114, 3519-3523; Angew. Chem. Int. Ed. 2002, 41, 3371-3375;
2. For some recent examples, see: a) C.-Y. Su, Y.-P. Cai, C.-L. Chen, F. Lissner, B.-S. Kang, W. Kaim, Angew. Chem. 2002, 114, 3519-3523; Angew. Chem. Int. Ed. 2002, 41, 3371-3375;
3. b) O. Hayashida, A. Shivanyuk, J. Rebek, Jr., Angew. Chem. 2002, 114, 3573-3576; Angew. Chem. Int. Ed. 2002, 41, 2423-2426;
4. b) O. Hayashida, A. Shivanyuk, J. Rebek, Jr., Angew. Chem. 2002, 114, 3573-3576; Angew. Chem. Int. Ed. 2002, 41, 2423-2426;
5. c) P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light, M. B. Hursthouse, J. Am. Chem. Soc. 2002, 124, 1128-1129;
6. d) M. Kercher, B. König, H. Zieg, L. De Cola, J. Am. Chem. Soc. 2002, 124, 11541-11551;
7. e) A. Marquis, J.-P. Kintzinger, R. Graff, P. N. N. Baxter, J.-M. Lehn, Angew. Chem. 2002, 114, 2884-2888; Angew. Chem. Int. Ed. 2002, 41, 2760-2764;
8. e) A. Marquis, J.-P. Kintzinger, R. Graff, P. N. N. Baxter, J.-M. Lehn, Angew. Chem. 2002, 114, 2884-2888; Angew. Chem. Int. Ed. 2002, 41, 2760-2764;
9. f) V. Paraschiv, M. Crego-Calama, T. Ishii, C. J. Padberg, P. Timmerman, D. N. Reinhoudt, J. Am. Chem. Soc. 2002, 124, 7638-7639;
10. g) M Aoyagi, S. Tashiro, M. Toominaga, K. Biradha, M. Fujita, Chem. Commun. 2002, 2036-2037;
11. h) C. A. Schalley, T. Muller, P. Linnartz, M. Witt, M. Schäfer, A. Lützen, Chem. Eur. J. 2002, 8, 3538-3551;
12. i) G. R. Newkome, T. J. Cho, C. N. Moorefield, R. Cush, P. S. Russo, L. A. Gordínez, M. J. Saunders, P. Mohaparta, Chem. Eur. J. 2002, 8, 2946-2954;
13. j) V. Percec, T. K. Bera, M. Glodde, Q. Fu, V. S. K. Balagurusamy, P. A. Heiney, Chem. Eur. J. 2003, 9, 921-935;
14. k) E. Mertz, S. C. Zimmerman, J. Am. Chem. Soc. 2003, 125, 3424-3425;
15. j) T. Ishi-i, M. A. Mateos-Timoneda, P. Timmerman, M. Crego-Calama, D. N. Reinhoudt, S. Shinkai, Angew. Chem. 2003, 115, 2402-2407; Angew. Chem. Int. Ed. 2003, 42, 2300-2305;
16. j) T. Ishi-i, M. A. Mateos-Timoneda, P. Timmerman, M. Crego-Calama, D. N. Reinhoudt, S. Shinkai, Angew. Chem. 2003, 115, 2402-2407; Angew. Chem. Int. Ed. 2003, 42, 2300-2305;
17. k) A. Wu, L. Isaacs, J. Am. Chem. Soc. 2003, 125, 4831-4835;
18. l) W. S. Horne, D. C. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2003, 125, 9372-9376;
19. m) P. Zhu, H. Kang, A. Facchetti, G. Evmenenko, P. Dutta, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 11496-11497.
20. a) M. Simard, S. Du, J. D. Wuest, J. Am. Chem. Soc. 1991, 113, 4696-4698;
21. b) X. Wang, M. Simard, J. D. Wuest, J. Am. Chem. Soc. 1994, 116, 12119-12120;
22. c) P. Brunet, M. Simard, J. D. Wuest, J. Am. Chem. Soc. 1997, 119, 2737-2738;
23. d) J-H. Fournier, T. Maris, J. D. Wuest, W. Guo, E. Galoppini, J. Am. Chem. Soc. 2003, 125, 1002-1006.
24. a) A. G. Kolchinski, D. H. Busch, N. W. Alcock, J. Chem. Soc. Chem. Commun. 1995, 1289-1291;
25. b) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001; Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869;
26. b) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001; Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869;
27. c) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004; Angew. Chem. Int. Ed. Engl. 1995, 34, 1869-1871;
28. c) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004; Angew. Chem. Int. Ed. Engl. 1995, 34, 1869-1871;
29. d) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
30. Pseudorotaxanes are complexes (supermolecules) that resemble rotaxanes by virtue of being comprised of wheel- and axlelike components, but their components are free to dissociate from each other. See: P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679.
31. F. M. Raymo, M. D. Bartberger, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc., 2001, 123, 9246-9267.
32. a) P. T. Glink, C. Schiavo, J. F. Stoddart, D. J. Williams, Chem. Commun. 1996, 1483-1490;
33. b) M. C. T. Fyfe, J. F. Stoddart, Adv. Supramol. Chem. 1999, 5, 1-53;
34. c) T. J. Hubin, A. G. Kolchinski, A. L. Vance, D. H. Busch, Adv. Supramol. Chem. 1999, 5, 237-357;
35. d) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5-52;
36. e) M. C. T. Fyfe, J. F. Stoddart, D. J. Williams, Struct. Chem. 1999, 10, 243-259;
37. f) S. J. Cantrill, A. R. Pease, J. F. Stoddart, J. Chem. Soc. Dalton Trans. 2000, 3715-3734.
38. a) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 59-62;
39. a) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 59-62;
40. b) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 760-763; Angew. Chem. Int. Ed. Engl. 1997, 36, 735-739;
41. b) P. R. Ashton, A. N. Collins, M. C. T. Fyfe, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 760-763; Angew. Chem. Int. Ed. Engl. 1997, 36, 735-739;
42. c) M. C. Feiters, M. C. T. Fyfe, M.-V. Martínez-Díaz, S. Menzer, R. J. M. Nolte, J. F. Stoddart, P. J. M. van Kan, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 8119-8120;
43. d) P. R. Ashton, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 12514-12524;
44. e) P. R. Ashton, M. C. T. Fyfe, S. K. Hickingbottom, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 577-589;
45. f) P. R. Ashton, M. C. T. Fyfe, M.-V. Martínez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534;
46. g) M. C. T. Fyfe, J. F. Stoddart, Coord. Chem. Rev. 1999, 183, 139-155;
47. h) J.-C. Meillon, N. Voyer, E. Biron, F. Sanschagrin, J. F. Stoddart, Angew. Chem. 2000, 112, 147-149; Angew. Chem. Int. Ed. 2000, 39, 143-145;
48. h) J.-C. Meillon, N. Voyer, E. Biron, F. Sanschagrin, J. F. Stoddart, Angew. Chem. 2000, 112, 147-149; Angew. Chem. Int. Ed. 2000, 39, 143-145;
49. i) M. V. Martínez-Díaz, M. S. Rodriguez-Morgade, M. C. Feiters, P. J. M. van Kan, R. J. M. Nolte, J. F. Stoddart, T. Torres, Org. Lett. 2000, 2, 1057-1060;
50. j) T. Chang, A. M. Heiss, S. J. Cantrill, M. C. T. Fyfe, A. R. Pease, S. J. Rowan, J. F. Stoddart, D. J. Williams, Org. Lett. 2000, 2, 2943-2946;
51. k) S.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2002, 114, 280-284; Angew. Chem. Int. Ed. 2002, 41, 270-274.
52. k) S.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2002, 114, 280-284; Angew. Chem. Int. Ed. 2002, 41, 270-274.
53. a) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
54. a) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
55. b) R. T. Lee, Y. C. Lee, Glyconjugate J. 2000, 17, 543-551;
56. c) P. I. Kitov, J. M. Sadawska, G. Mulvey, G. D. Armstrong, H. Ling, N. S. Pannu, R. J. Read, D. R. Bundle, Nature 2000, 403, 669-672;
57. d) M. Mourez, R. S. Kane, J. Mogridge, S. Metallo, P. Deschatelets, B. R. Sellman, G. M. Whitesides, R. J. Collier, Nature Biotechnology 2001, 19, 958-961;
58. e) C. W. Cairo, J. E. Gestwicki, M. Kanai, L. L. Kiessling, J. Am. Chem. Soc. 2002, 124, 1615-1619;
59. f) J. E. Gestwicki, C. W. Cairo, L. E. Strong, K. A. Oetjen, L. L. Kiessling, J. Am. Chem. Soc. 2002, 124, 14922-14933;
60. g) J. J. Lundquist, E. J. Toone, Chem. Rev. 2002, 102, 555-578;
61. h) T. Christensen, D. M. Gooden, J. E. Kung, E. J. Toone, J. Am. Chem. Soc. 2003, 125, 7357-7366;
62. i) E. Arranz-Plaza, A. S. Tracy, A. Siriwardena, J. M. Pierce, G.-J. Boons, J. Am. Chem. Soc. 2002, 124, 13035-13046;
63. j) E. K. Woller, E. D. Walter, J. R. Morgan, D. J. Singel, M. J. Cloninger, J. Am. Chem. Soc. 2003, 125, 8820-8826;
64. k) S. L. Tobey, E. V. Anslyn, J. Am. Chem. Soc. 2003, 125, 10963-10970;
65. l) P. I. Kitov, D. R. Bundle, J. Am. Chem. Soc. 2003, 125, 16271-16284;
66. m) G. Ercolani, J. Am. Chem. Soc. 2003, 125, 16097-16103;
67. n) D. A. Fulton, S. J. Cantrill, J. F. Stoddart, J. Org. Chem. 2002, 67, 7968-7981;
68. o) J. N. Lowe, D. A. Fulton, S.-H. Chiu, A. M. Elizarov, S. J. Cantrill, S. J. Rowan, J. F. Stoddart, J. Org. Chem. 2004, 69, in press;
69. p) J. D. Badjić, S. J. Cantrill, J. F. Stoddart, J. Am. Chem. Soc. 2004, 126, in press.
70. a) P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347; Angew. Chem. Int. Ed. 1998, 37, 4295-4307;
71. a) P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347; Angew. Chem. Int. Ed. 1998, 37, 4295-4307;
72. b) S. J. Cantrill, G. J. Youn, J. F. Stoddart, D. J. Williams, J. Org. Chem. 2001, 66, 6857-6872;
73. c) S.-H. Chiu, S. J. Rowan, S. J. Cantrill, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 2002, 2948-2949.
74. a) M. C. T. Fyfe, J. N. Lowe, J. F. Stoddart, D. J. Williams, Org. Lett. 2000, 2, 1221-1224;
75. b) V. Balzani, M. Clemente-Leon, A. Credi, J. N. Lowe, J. D. Badjić, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 2003, 9, 5348-5360.
76. It has been noted that another trivalent system, namely tris(vancomycin carboxamide) binds a trivalent ligand derived from D-Ala-D-Ala with much higher affinity than avadin binds biotin. See: J. Rao, J. Lahiri, L. Isaacs, R. M. Weis, G. M. Whitesides, Science 1998, 280, 708-711. In the abstract to this article the authors state "High affinity trivalent binding and monovalent binding are fundamentally different. In trivalent (and more generally, polyvalent) binding, dissociation occurs in stages, and its rate can be accelerated by monovalent ligands at sufficiently high concentrations. In monovalent binding, dissociation is determined solely by the rate constant for dissociation and cannot be accelerated by added monomer."
77. a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
78. a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530; Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
79. b) V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nano World, Wiley-VCH, Weinheim, 2003.
80. For an example of working supramolecular machines in the form of [2]pseudorotaxanes trapped in glass and mounted on the surface of silica films, see: a) S. Chia, J. Cao, J. F. Stoddart, J. I. Zink, Angew. Chem. 2001, 113, 2513-2517; Angew. Chem. Int. Ed. 2001, 40, 2447-2451;
81. For an example of working supramolecular machines in the form of [2]pseudorotaxanes trapped in glass and mounted on the surface of silica films, see: a) S. Chia, J. Cao, J. F. Stoddart, J. I. Zink, Angew. Chem. 2001, 113, 2513-2517; Angew. Chem. Int. Ed. 2001, 40, 2447-2451;
82. for a recent example where a [2]pseudorotaxane, as a self-assembled monolayer on gold, has been shown to undergo reversible dethreading and rethreading of its ring, and to exhibit ion gating behavior, see: b) K. Kim, W. S. Jeon, J.-K. Kang, J. W. Lee, S. Y. Jon, T. Kim, K. Kim, Angew. Chem. 2003, 115, 2395-2398; Angew. Chem. Int. Ed. 2003, 42, 2293-2296;
83. for a recent example where a [2]pseudorotaxane, as a self-assembled monolayer on gold, has been shown to undergo reversible dethreading and rethreading of its ring, and to exhibit ion gating behavior, see: b) K. Kim, W. S. Jeon, J.-K. Kang, J. W. Lee, S. Y. Jon, T. Kim, K. Kim, Angew. Chem. 2003, 115, 2395-2398; Angew. Chem. Int. Ed. 2003, 42, 2293-2296;
84. for examples of acid-base switchable [2]rotaxanes which have been demonstrated to switch in solution, see: c) M. V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 1904-1907;
85. for examples of acid-base switchable [2]rotaxanes which have been demonstrated to switch in solution, see: c) M. V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 1904-1907;
86. d) P. R. Ashton, R. Ballardini, V. Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi, M. Gómez-López, M. V. Martí nez-Díaz, A. Piersanti, N. Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 11932-11942;
87. e) A. M. Elizarov, S.-H. Chiu, J. F. Stoddart, J. Org. Chem. 2002, 67, 9175-9181.
88. Supramolecular Polymers (Ed.: A. Ciferri), Marcel Deker, New York, 2000.
89. a) D. H. Busch, N. A. Stephensen, Coord. Chem. Rev. 1990, 100, 119-154;
90. b) S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475;
91. c) R. Cacciapaglia, L. Mandolini, Chem. Soc. Rev. 1993, 22, 221-231;
92. d) R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398; Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384;
93. d) R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398; Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384;
94. e) Templated Organic Synthesis (Eds.: F. Diederich, P.J. Stang), Wiley-VCH, Weinheim, 2000;
95. f) J. F. Stoddart, H.-R. Tseng, Proc. Natl. Acad. Sci. USA 2002, 99, 4797-4800.
96. a) R. F. Service, Science 2001, 291, 426-427;
97. b) R. F. Service, Science 2001, 294, 2442-2443;
98. c) A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Res. 2001, 34, 433-434;
99. d) A. R. Pease, J. F. Stoddart, Struct. Bonding 2001, 99, 189-236;
100. e) J. R. Heath, M. A. Ratner, Phys. Today 2003, 56, 43-49.
101. a) C. P. Collier, E. W. Wong, M. Belohradsky, F. M. Raymo, J.F. Stoddart, P. J. Kuekes, R. S. Williams, J. R. Heath, Science 1999, 285, 391-394;
102. b) E. W. Wong, C. P. Collier, M. Belohradsky, F. M. Raymo, J. F. Stoddart, J. R. Heath, J. Am. Chem. Soc. 2000, 122, 5831-5840;
103. c) C. P. Collier, G. Mattersteig, E. W. Wong, Y. Luo, K. Beverly, J. Sampaio, F. M. Raymo, J. F. Stoddart, J. F. Heath, Science 2000, 289, 1172-1175;
104. d) C. P. Collier, J. O. Jeppensen, Y. Luo, J. Perkins, E. W. Wong, J. R. Heath, J. F. Stoddart, J. Am. Chem. Soc. 2001, 123, 12632-12641;
105. e) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. DeIonno, G. Ho, J. Perkins, H.-R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, ChemPhysChem 2002, 3, 519-525;
106. f) M. R. Diehl, D. W. Steuerman, H.-R. Tseng, S. A. Vignon, A. Star, P. C. Celestre, J. F. Stoddart, J. R. Heath, ChemPhysChem 2003, 4, 1335-1339;
107. g) H. Yu, Y. Luo, K. Beverly, H.-R. Tseng, J. F. Stoddart, J. R. Heath, Angew. Chem. 2003, 115, 5884-5889; Angew. Chem. Int. Ed. 2003, 42, 5706-5711;
108. g) H. Yu, Y. Luo, K. Beverly, H.-R. Tseng, J. F. Stoddart, J. R. Heath, Angew. Chem. 2003, 115, 5884-5889; Angew. Chem. Int. Ed. 2003, 42, 5706-5711;
109. h) H.-R. Tseng, D. Wu, N. X. Fang, X. Zhang, J. F. Stoddart, ChemPhysChem 2004, 5, 111-116.
110. We have introduced and used the term co-conformation to designate the three-dimensional spatial arrangements of 1) the constituent parts of supramolecular systems and 2) the components of interlocked molecular systems See M. C. T. Fyfe, J. F. Stoddart, Acc. Chem. Res. 1997, 30, 393-401.
111. G. A. Julia, M. A. Garcia, A. J. Benesi, T. E. Mallouk, J. Org. Chem. 1998, 63, 7663-7669.
112. [1,3]-Dipolar cycloadditions have already been used successfully in the template-directed synthesis of [2]-rotaxanes, using a threading-followed-by-stoppering approach See a) P. R. Ashton, P. T. Glink, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 729-736;
113. b) J. Cao, M. C. T. Fyfe, J. F. Stoddart, G. R. L. Cousins, P. T. Glink, J. Org. Chem. 2000, 65, 1937-1946.
114. [1,3]-Dipolar cycloadditions are among a group of highly efficient reactions which have earned them the status of so-called "click chemistry" reactions See: H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
115. [1,3]-Dipolar cycloadditions are among a group of highly efficient reactions which have earned them the status of so-called "click chemistry" reactions See: H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
116. S. T. Abu-Orabi, M. A. Atfah, I. Jibril, F. M. Mari'i, A. A. S. Ali, J. Heterocycl. Chem. 1989, 26, 1461-1468.
117. 1H NMR spectroscopy, all the indications are that one major product is formed with complete conversion of the starting material.
118. a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. M. Kern, J. Am. Chem. Soc. 1984, 106, 3043-3045;
119. b) D. B. Amabilino, C. O. Dietrich-Buchecker, A. Livoreil, L. Peréz-García, J.-P. Sauvage, J. F. Stoddart, J. Am. Chem. Soc. 1996, 118, 3905-3913;
120. c) D. J. Cardenas, A. Livoreil, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 11980-11981;
121. d) L. Raehm, J.-M. Kern, J.-P. Sauvage, Chem. Eur. J. 1999, 5, 3310-3317;
122. e) C. O. Dietrich-Buchecker, B. Colasson, M. Fujita, A. Hori, N. Geum, S. Sakamoto, K. Yamaguchi, J.-P. Sauvage, J. Am. Chem. Soc. 2003, 125, 5717-5725.
123. M. Montalti, R. Ballardini, L. Prodi, V. Balzani, Chem. Commun. 1996, 2011-2012;
124. b) P. R. Ashton, R. Ballardini, V. Balzani, M. Gómez-López, S. E. Lawrence, M.-V. Martínez-Díaz, M. Montalti, A. Piersanti, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 10641-10651;
125. c) P. R. Ashton, R. Ballardini, V. Balzani, M. C. T. Fyfe, M. T. Gandolfi, M.-V. Martínez-Díaz, M. Morosini, C. Schiavo, K. Shibata, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 2332-2341; E. Ishow, A. Credi, V. Balzani, H. D. A. Hoffman, M.-V. Martínez-Díaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482-3493.
126. c) P. R. Ashton, R. Ballardini, V. Balzani, M. C. T. Fyfe, M. T. Gandolfi, M.-V. Martínez-Díaz, M. Morosini, C. Schiavo, K. Shibata, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 2332-2341; E. Ishow, A. Credi, V. Balzani, H. D. A. Hoffman, M.-V. Martínez-Díaz, F. M. Raymo, J. F. Stoddart, M. Venturi, Chem. Eur. J. 2001, 7, 3482-3493.
127. -1. See references [10] and [11].
128. H.-J. Schneider, A. Yatsimirsky, Principles and Methods in Supramolecular Chemistry, Wiley, Chichester, 2000.
129. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy, K. R. A. S. Sandanayaka, Top. Curr. Chem. 1993, 168, 223-264.
130. P. T. Glink, A. J. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875.
131. P. T. Glink, A. J. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875.