En route to a molecular sheaf: Active metal template synthesis of a [3]rotaxane with two axles threaded through one ring

Journal of the American Chemical Society

Volumn 133, Issue 31, 2011, Pages 12298-12303

  Cheng, Hei Man ^a   Leigh, David A ^a   Maffei, Francesca ^a   McGonigal, Paul R ^a   Slawin, Alexandra M Z ^b   Wu, Jhenyi ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE METALS; ACTIVE TEMPLATE; ALKYL CHAIN; EN-ROUTE; END GROUPS; GENERAL METHOD; HOMOCOUPLING REACTIONS; MACROCYCLES; RING SIZES; ROTAXANES; TEMPLATE SYNTHESIS;

AXLES; METALS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

WHEELS;

MACROCYCLIC COMPOUND; METAL; NICKEL COMPLEX; ROTAXANE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; PARTICLE SIZE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 79961157517     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205167e     Document Type: Article

References (86)

1. Molecular Catenanes, Rotaxanes and Knots: A Journey through the World of Molecular Topology; Sauvage, J.-P., Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
2. Breault, G. A.; Hunter, C. A.; Mayers, P. C. Tetrahedron 1999, 55, 5265-5293
3. Raehm, L.; Hamilton, D. G.; Sanders, J. K. M. Synlett 2002, 1743-1761
4. Kim, K. Chem. Soc. Rev. 2002, 31, 96-107
5. Kay, E. R.; Leigh, D. A. Top. Curr. Chem. 2005, 262, 133-177
6. Tian, H.; Wang, Q. C. Chem. Soc. Rev. 2006, 35, 361-374
7. Bogdan, A.; Rudzevich, Y.; Vysotsky, M. O.; Böhmer, V. Chem. Commun. 2006, 2941-2952
8. Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103-112
9. Loeb, S. J. Chem. Soc. Rev. 2007, 36, 226-235
10. Dichtel, W. R.; Miljanić, O. Š.; Zhang, W.; Spruell, J. M.; Patel, K.; Aprahamian, I.; Heath, J. R.; Stoddart, J. F. Acc. Chem. Res. 2008, 41, 1750-1761
11. Faiz, J. A.; Heitz, V.; Sauvage, J.-P. Chem. Soc. Rev. 2009, 38, 422-442
12. Mullen, K. M.; Beer, P. D. Chem. Soc. Rev. 2009, 38, 1701-1713
13. Gassensmith, J. J.; Baumes, J. M.; Smith, B. D. Chem. Commun. 2009, 6329-6338
14. Gaviña, P.; Tatay, S. Curr. Org. Syn. 2010, 7, 24-43
15. Hänni, K. D.; Leigh, D. A. Chem. Soc. Rev. 2010, 39, 1240-1251
16. Qu, D.-H.; Tian, H. Chem. Sci. 2011, 2, 1011-1015
17. Amabilino, D. B.; Ashton, P. R.; Bělohradský, M.; Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 747-750
18. Amabilino, D. B.; Ashton, P. R.; Bělohradský, M.; Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 751-753
19. Amabilino, D. B.; Ashton, P. R.; Balzani, V.; Brown, C. L.; Credi, A.; Fréchet, J. M. J.; Leon, J. W.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 1996, 118, 12012-12020
20. Solladié, N.; Chambron, J. C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Angew. Chem., Int. Ed. 1996, 35, 906-909
21. Amabilino, D. B.; Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Bělohradský, M.; Credi, A.; Higuchi, M.; Raymo, F. M.; Shimizu, T.; Stoddart, J. F.; Venturi, M.; Yase, K. New J. Chem. 1998, 22, 959-972
22. Solladié, N.; Chambron, J. C.; Sauvage, J.-P. J. Am. Chem. Soc. 1999, 121, 3684-3692
23. Parham, A. H.; Schmieder, R.; Vögtle, F. Synlett 1999, 1887-1890
24. Watanabe, N.; Yagi, T.; Kihara, N.; Takata, T. Chem. Commun. 2002, 2720-2721
25. Tuncel, D.; Steinke, J. H. G. Chem. Commun. 2002, 496-497
26. Dichtel, W. R.; Miljanić, O. Š.; Spruell, J. M.; Heath, J. R.; Stoddart, J. F. J. Am. Chem. Soc. 2006, 128, 10388-10390
27. Tuncel, D.; Cindir, N.; Koldemir, U. J. Inclusion Phenom. Macrocyclic Chem. 2006, 55, 373-380
28. Wu, J.; Leung, K. C. F.; Stoddart, J. F. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 17266-17271
29. Taira, T.; Suzaki, Y.; Osakada, K. Chem. Asian J. 2008, 3, 895-902
30. Frey, J.; Tock, C.; Collin, J. P.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 2008, 130, 4592-4593
31. Li, S. J.; Liu, M.; Zhang, J. Q.; Zheng, B.; Wen, X. H.; Li, N.; Huang, F. H. Eur. J. Org. Chem. 2008, 6128-6133
32. Marois, J.-S.; Cantin, K.; Desmarais, A.; Morin, J.-F. Org. Lett. 2008, 10, 33-36
33. Collin, J. P.; Frey, J.; Heitz, V.; Sauvage, J. P.; Tock, C.; Allouche, L. J. Am. Chem. Soc. 2009, 131, 5609-5620
34. Wang, J. Y.; Han, J. M.; Yan, J.; Ma, Y. G.; Pei, J. Chem.- Eur. J. 2009, 15, 3585-3594
35. Iwamoto, H.; Yawata, Y.; Fukazawa, Y.; Haino, T. Chem. Lett. 2009, 39, 24-25
36. Belowich, M. E.; Valente, C.; Stoddart, J. F. Angew. Chem., Int. Ed. 2010, 49, 7208-7212
37. Li, S.; Zheng, B.; Chen, J.; Dong, S.; Ma, Z.; Huang, F.; Gibson, H. W. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 4067-4073
38. Yin, J.; Dasgupta, S.; Wu, J. Org. Lett. 2010, 12, 1712-1715
39. Yin, J.; Chi, C.; Wu, J. Org. Biomol. Chem. 2010, 8, 2594-2599
40. Collin, J.-P.; Durot, S.; Keller, M.; Sauvage, J.-P.; Trolez, Y.; Cetina, M.; Rissanen, K. Chem.- Eur. J. 2011, 17, 947-957
41. Basu, S.; Coskun, A.; Friedman, D. C.; Olson, M. A.; Benítez, D.; Tkatchouk, E.; Barin, G.; Yang, J.; Fahrenbach, A. C.; Goddard, W. A.; Stoddart, J. F. Chem.- Eur. J. 2011, 17, 2107-2119
42. Kohsaka, Y.; Nakazono, K.; Koyama, Y.; Asai, S.; Takata, T. Angew, Chem. Int. Ed. 2011, 50, 4872-4875
43. For recent reviews on polymeric rotaxanes with multiple rings encircling linear or branched threads, see: Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Chem. Rev. 2009, 109, 5974-6023
44. Fang, L.; Olson, M. A.; Benítez, D.; Tkatchouk, E.; Goddard, W. A.; Stoddart, J. F. Chem. Soc. Rev. 2010, 39, 17-29
45. Leung, K. C.-F.; Lau, K.-N. Polym. Chem. 2010, 1, 988-1000
46. Klotz, E. J. F.; Claridge, T. D. W.; Anderson, H. L. J. Am. Chem. Soc. 2006, 128, 15374-15375
47. Prikhodko, A. I.; Durola, F.; Sauvage, J.-P. J. Am. Chem. Soc. 2008, 130, 448-449
48. Prikhodko, A.; Sauvage, J.-P. J. Am. Chem. Soc. 2009, 131, 6794-6807
49. Lee, C. F.; Leigh, D. A.; Pritchard, R. G.; Schultz, D.; Teat, S. J.; Timco, G. A.; Winpenny, R. E. P. Nature 2009, 458, 314-318
50. Ackermann, D.; Schmidt, T. L.; Hannam, J. S.; Purohit, C. S.; Heckel, A.; Famulok, M. Nat. Nanotechnol. 2010, 5, 436-442
51. Cucurbit[8]uril can form pseudo[3]rotaxane-like ternary supramolecular complexes with two guests bound within its cavity, see: Kim, J.; Jung, I.; Kim, S.; Lee, E.; Kang, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540-541 This phenomenon has been exploited to make: supramolecular "necklaces": Ko, Y.; Kim, K.; Kang, J.; Chun, H.; Lee, J.; Sakamoto, S.; Yamaguchi, K.; Fettinger, J.; Kim, K. J. Am. Chem. Soc. 2004, 126, 1932-1933
52. supramolecular block co-polymers: Rauwald, U.; Scherman, O. A. Angew. Chem., Int. Ed. 2008, 47, 3950-3953 and cross-linked networks: Appel, E. A.; Biedermann, F.; Rauwald, U.; Jones, S. T.; Zayed, J. M.; Scherman, O. A. J. Am. Chem. Soc. 2010, 132, 14251-14260
53. supramolecular protein-polymer conjugates, Biedermann, F.; Rauwald, U.; Zayed, J. M.; Scherman, O. A. Chem. Sci. 2011, 2, 279-286 and, supramolecular gold nanoparticle-polymer composites, Coulston, R. J.; Jones, S. T.; Lee, T. C.; Appel, E. A.; Scherman, O. A. Chem. Commun. 2011, 47, 164-166 γ-Cyclodextrin and some crown ethers can also bind two substrates within their cavities, see: Ueno, A.; Takahashi, K.; Osa, T. J. Chem. Soc., Chem. Commun. 1980, 921-922
54. Herrmann, W.; Wehrle, S.; Wenz, G. Chem. Commun. 1997, 1709-1710
55. Herrmann, W.; Schneider, M.; Wenz, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2511-2514
56. Roa, K. S. S. P.; Hubig, S. M.; Moorthy, J. N.; Kochi, J. K. J. Org. Chem. 1999, 64, 8098-8104
57. Chiu, S.-H.; Pease, A. R.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 2002, 41, 270-274
58. The ternary supramolecular complexes cited in ref 5 are all thermodynamically stable with respect to their decomplexed components, but kinetically labile in solution (the guests undergo exchange with others in the bulk). In contrast, [3]rotaxane 5 - which is a molecule not a supramolecular complex (Hannam, J. S.; Lacy, S. M.; Leigh, D. A.; Saiz, C. G.; Slawin, A. M. Z.; Stitchell, S. G. Angew. Chem., Int. Ed. 2004, 43, 3260-3264)- is kinetically stable to dethreading but, with no significant favorable interactions between the components, certainly thermodynamically unstable with respect to its non-interlocked components
59. Saito, S.; Nakazono, K.; Takahashi, E. J. Org. Chem. 2006, 71, 7477-7480
60. Aucagne, V.; Hänni, K. D.; Leigh, D. A.; Lusby, P. J.; Walker, D. B. J. Am. Chem. Soc. 2006, 128, 2186-2187
61. Saito, S.; Takahashi, E.; Nakazono, K. Org. Lett. 2006, 8, 5133-5136
62. Crowley, J. D.; Hänni, K. D.; Lee, A.-L.; Leigh, D. A. J. Am. Chem. Soc. 2007, 129, 12092-12093
63. Aucagne, V.; Berná, J.; Crowley, J. D.; Goldup, S. M.; Hänni, K. D.; Leigh, D. A.; Lusby, P. J.; Ronaldson, V. E.; Slawin, A. M. Z.; Viterisi, A.; Walker, D. B. J. Am. Chem. Soc. 2007, 129, 11950-11963
64. Berná, J.; Crowley, J. D.; Goldup, S. M.; Hänni, K. D.; Lee, A. L.; Leigh, D. A. Angew. Chem., Int. Ed. 2007, 46, 5709-5713
65. Goldup, S. M.; Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Slawin, A. M. Z. Angew. Chem., Int. Ed. 2008, 47, 3381-3384
66. Berná, J.; Goldup, S. M.; Lee, A.-L.; Leigh, D. A.; Symes, M. D.; Teobaldi, G.; Zerbetto, F. Angew. Chem., Int. Ed. 2008, 47, 4392-4396
67. Sato, Y.; Yamasaki, R.; Saito, S. Angew. Chem., Int. Ed. 2008, 48, 504-507
68. Crowley, J. D.; Goldup, S. M.; Lee, A. L.; Leigh, D. A.; McBurney, R. T. Chem. Soc. Rev. 2009, 38, 1530-1541
69. Goldup, S. M.; Leigh, D. A.; Long, T.; McGonigal, P. R.; Symes, M. D.; Wu, J. J. Am. Chem. Soc. 2009, 131, 15924-15929
70. Goldup, S. M.; Leigh, D. A.; McGonigal, P. R.; Ronaldson, V. E.; Slawin, A. M. Z. J. Am. Chem. Soc. 2010, 132, 315-320
71. Crowley, J. D.; Hänni, K. D.; Leigh, D. A.; Slawin, A. M. Z. J. Am. Chem. Soc. 2010, 132, 5309-5314
72. Crowley, J. D.; Goldup, S. M.; Gowans, N. D.; Leigh, D. A.; Ronaldson, V. E.; Slawin, A. M. Z. J. Am. Chem. Soc. 2010, 132, 6243-6248
73. Goldup, S. M.; Leigh, D. A.; McBurney, R. T.; McGonigal, P. R.; Plant, A. Chem. Sci. 2010, 1, 383-386
74. Lahlali, H.; Jobe, K.; Watkinson, M.; Goldup, S. M. Angew. Chem., Int. Ed. 2011, 51, 4151-4155
75. For [ n ]rotaxanes synthesized using fewer than n -1 template sites, see: Fuller, A. M. L.; Leigh, D. A.; Lusby, P. J. Angew. Chem., Int. Ed. 2007, 46, 5015-5019
76. Fuller, A.-M. L.; Leigh, D. A.; Lusby, P. J. J. Am. Chem. Soc. 2010, 132, 4954-4959
77. Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 46, 5743-5745
78. Kim, H.; Lee, C. Org. Lett. 2011, 13, 2050-2053
79. Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138-2141
80. In general, free 2,2′:6′,2″-terpyridine ligands preferentially adopt a trans-trans geometry. When acting as a tridentate ligand, rotation around the 2,2′- and 6′,2″ bonds occurs to give the coordinating cis-cis geometry, see: Bazzicalupi, C.; Bencini, A.; Bianchi, A.; Danesi, A.; Faggi, E.; Giorgi, C.; Santarelli, S.; Valtancoli, B. Coord. Chem. Rev. 2008, 252, 1052-1068
81. An optimized 46% yield of [2]rotaxane was reported in ref 8n using the bisoxazoline macrocycle and 2.2 equiv of alkyl bromide at room temperature in DMF. In the present study with the terpyridyl-macrocycle (1), the use of a 1:1 mixture of THF-NMP enabled all of the reactants to be in solution at the start of the reaction. Heating to 60 °C was necessary to allow reactions with >5 equiv of 2 to reach completion within 18 h. The proportion of interlocked and non-interlocked products was unchanged when the reactions were carried out with DMF as solvent and/or at room temperature (other conditions as for Table 1, entry 2).
82. Two-ring-one-thread [3]rotaxanes have previously been observed as byproducts in Cu-catalyzed azide-alkyne cycloaddition (CuAAC) active metal template reactions, see ref 8d.
83. Loren, J. C.; Yoshizawa, M.; Haldiman, R.; Linden, A.; Siegel, J. S. Angew. Chem., Int. Ed. 2003, 42, 5702-5705
84. Forgan, R. S.; Spruell, J. M.; Olsen, J.-C.; Stern, C. L.; Stoddart, J. F. J. Mex. Chem. Soc. 2009, 53, 134-138
85. Forgan, R. S.; Friedman, D. C.; Stern, C. L.; Bruns, C. J.; Stoddart, J. F. Chem. Commun. 2010, 46, 5861-5863
86. A "sheaf" (plural: sheaves) is a bundle of objects held together by a band or other mechanical binder. Familiar examples include the way that wheat, rye, and other cereals are traditionally bound with straw or twine after reaping.