Oligocatenanes made to order

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4295-4307

  Amabilino, David B ^a,e   Ashton, Peter R ^a   Balzani, Vincenzo ^c,d   Boyd, Sue E ^a   Credi, Alberto ^c   Lee, Ju Young ^a   Menzer, Stephan ^b   Stoddart, J Fraser ^a,d   Venturi, Margherita ^c   Williams, David J ^b,d  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHER DERIVATIVE; MACROCYCLIC COMPOUND; POLYETHER DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; HYDROGEN BOND; ISOMER; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 0032513696     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9720873     Document Type: Article

References (69)

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2. For comprehensive reviews on catenanes, see: (a) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (c) Jäger. R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930-944.
3. For comprehensive reviews on catenanes, see: (a) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (c) Jäger. R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930-944.
4. For comprehensive reviews on catenanes, see: (a) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 87, 795-810. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (c) Jäger. R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930-944.
5. For a recent communication on catenanes, see: Hamilton, D. G.; Feeder, N.; Prodi, L.; Teat, S. J.; Clegg, W.; Sanders, J. K. M. J. Am. Chem. Soc. 1998, 120, 1096-1097.
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11. See, for example: (a) Walba, D. M.; Zheng, Q. Y.; Schilling, K. J. Am. Chem. Soc. 1992, 114, 6259-6260. (b) Nierengarten, J.-F.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. New J. Chem. 1996, 20, 685-693.
12. See, for example: (a) Walba, D. M.; Zheng, Q. Y.; Schilling, K. J. Am. Chem. Soc. 1992, 114, 6259-6260. (b) Nierengarten, J.-F.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. New J. Chem. 1996, 20, 685-693.
13. For an example of higher catenanes based on metal-ion templated synthesis, see: Dietrich-Buchecker, C. O.; Frommberger, B.; Lüer, I.; Sauvage, J.-P.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1434-1437.
14. Amabilino, D. B.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 2351-2359.
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16. (a) Geerts, Y.; Muscat, D.; Müllen, K. Macromol. Chem. Phys. 1995, 796, 3425-3435.
17. (b) Menzer, S.; White, A. J. P.; Williams, D. J.; Belohradsky, M.; Hamers, C.; Raymo, F. M.; Shipway, A. N.; Stoddart, J. F. Macromolecules 1998, 31, 295-307.
18. Some not so convincing reports on linear polycatenanes have appeared in the literature at a time when the analytical techniques available for characterizing these compounds were not so sophisticated. For a lead article, see: Karagounis, G.; Pandi-Agathokli, I.; Kontaraki, E. IUPAC Colloid & Interface Sci. International Conf. 1975, 1, 671-678.
19. Stoddart, J. F. Nature 1988, 334, 10-11.
20. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
21. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
22. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
23. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
24. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
25. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
26. Relatively poorly defined macromolecular systems that can be regarded as polycatenanes have been prepared. They show interesting properties when compared with their noninterlocked components. See, for example: (a) Millar, J. R. J. Chem. Soc. 1960, 1311-1317. (b) Garrido, L.; Mark, J. E.; Clarson, S. J.; Semlyen, J. A. Polym. Commun. 1985, 26, 55-57. A number of crystalline solids contain interlocked rings which are formed in the process of crystallization. However, their superstructures do not persist in solution. For pertinent articles on related solids with references therein, see: (c) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (d) Stumpf, H. O.; Ouahab, L.; Pei, Y.; Grandjean, D.; Kahn, O. Science 1993, 261, 447-449. (e) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287-7288. (f) Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. Chem. Commun. 1996, 1313-1314. (g) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765-771.
27. For reviews discussing π-π stacking, see, along with references therein: (a) Dahl, T. Acta Chem. Scand. 1994, 48, 95-106. (b) Hunter, C. A. Chem. Soc. Rev. 1994. 101-109. In the case of the types of compounds we are concerned with in this paper, the π-π stacking leads to charge-transfer bands in the visible region of the electronic absorption spectrum. For a review concerning interactions between neutral donors and charged acceptors, see: Kamper, V. E. Russ. Chem. Rev. 1982, 51, 107-118. For a review on charge-transfer interactions in cyclophanes, see: Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35.
28. For reviews discussing π-π stacking, see, along with references therein: (a) Dahl, T. Acta Chem. Scand. 1994, 48, 95-106. (b) Hunter, C. A. Chem. Soc. Rev. 1994. 101-109. In the case of the types of compounds we are concerned with in this paper, the π-π stacking leads to charge-transfer bands in the visible region of the electronic absorption spectrum. For a review concerning interactions between neutral donors and charged acceptors, see: Kamper, V. E. Russ. Chem. Rev. 1982, 51, 107-118. For a review on charge-transfer interactions in cyclophanes, see: Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35.
29. For reviews discussing π-π stacking, see, along with references therein: (a) Dahl, T. Acta Chem. Scand. 1994, 48, 95-106. (b) Hunter, C. A. Chem. Soc. Rev. 1994. 101-109. In the case of the types of compounds we are concerned with in this paper, the π-π stacking leads to charge-transfer bands in the visible region of the electronic absorption spectrum. For a review concerning interactions between neutral donors and charged acceptors, see: Kamper, V. E. Russ. Chem. Rev. 1982, 51, 107-118. For a review on charge-transfer interactions in cyclophanes, see: Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35.
30. For reviews discussing π-π stacking, see, along with references therein: (a) Dahl, T. Acta Chem. Scand. 1994, 48, 95-106. (b) Hunter, C. A. Chem. Soc. Rev. 1994. 101-109. In the case of the types of compounds we are concerned with in this paper, the π-π stacking leads to charge-transfer bands in the visible region of the electronic absorption spectrum. For a review concerning interactions between neutral donors and charged acceptors, see: Kamper, V. E. Russ. Chem. Rev. 1982, 51, 107-118. For a review on charge-transfer interactions in cyclophanes, see: Schwartz, M. H. J. Inclusion Phenom. 1990, 9, 1-35.
31. Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
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35. Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams. D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197.
36. Ashton, P. R.; Brown, C. L.; Chrystal, E. J. T.; Goodnow, T. T.; Kaifer, A. E.; Parry, K. P.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1039-1042.
37. Ashton. P. R.; Huff, J.; Menzer, S.; Parsons, I. W.; Preece, J. A.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 31-44.
38. Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 433-437.
39. Amabilino, D. B.; Ashton, P. R.; Brown, C. L.; Córdova, E.; Godínez, L.; Goodnow, T. T.; Kaifer, A. E.; Newton, S. P.; Pietraszkiewicz, M.; Philp, D.; Raymo, F. M.; Reder, A. S.; Rutland, M. T.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 1271-1293.
40. The binding constants for substrates containing 1,5-dioxynaphthalene ring systems with- and consequently their templating actions in the formation of-cyclobis(paraquat-p-phenylene) are known to be greater than those for those substrates containing hydroquinone rings. See: Ashton, P. R.; Blower, M.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Ballardini, R.; Ciano, M.; Balzani, V.; Gandolfi, M. T.; Prodi, L.; McLean, C. H. New J. Chem. 1993. 17. 689.
41. Asakawa, M.; Dehaen, W.; L'abbé, G.; Menzer, S.; Nouwen, J.; Raymo, F. M.; Stoddart, J. F.; Williams, D. J. J. Org. Chem. 1996, 61, 9591-9595.
42. Asakawa, M.; Ashton, P. R.; Menzer, S.; Raymo, F. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 877-893.
43. Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1286-1290.
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50. For a preview of the X-ray crystal structure of the heptacatenane, see: Amabilino, D. B.; Ashton, P. R.; Boyd, S. E.; Lee, J. Y.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2070-2072.
51. For a preliminary glimpse of the X-ray crystal structure of Olympiadane, see: Dagani, R. Chem. Eng. News 1996, Sept. 2, 31.
52. For a review discussing the "cesium effect" upon cyclizations, see: Ostrowicki, A.; Koepp, E.; Vögtle, F. Top. Curr. Chem. 1991, 161, 37-67.
53. Ashton, P. R.; Chrystal, E. J. T.; Mathias, J. P.; Parry, K. P.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Tetrahedron Lett, 1987, 28, 6367-6370.
54. This macrocyclic polyether (TN76C20) can be used as a template for the formation of cyclobis(paraquat-p-phenylene), leading to a variety of catenanes, which will be described elsewhere by: Amabilino, D. B.; Lee, J. Y.; Stoddart, J. F. Unpublished results.
55. Amabilino, D. B.; Ashton, P. R.; Stoddart, J. F.; Menzer, S.; Williams, D. J. J Chem. Soc., Chem. Commun. 1994, 2475-2478.
56. 6 does indeed act as a host for 1,5-dioxynaphthalene derivatives: Amabilino, D. B.; Stoddart, J. F. Unpublished results.
57. The highest yield achieved for a catenation involving this tetracationic cyclophane is 31%. It has been attained by using the macrocyclic polyether DN38C10 as a the template. The selectivity displayed for the formation of the [3]catenane in preference to the [2]catenane in the self-assembly process is less.for TN57C15 than for DN38C10. A similar phenomenon was observed for the hydroquinone ring-containing macrocyclic polyether templates.
58. Isaacs, N. S. Tetrahedron 1991, 47, 8463-8497.
59. Although the ring-closure reaction in this catenation is controlled by kinetics, the thermodynamics of binding clearly must play an initial role in the self-assembly process. See: Amabilino, D. B.; Ashton, P. R.; Pérez-García, L.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2378-2380.
60. In view of the limited resolution of the data, we have not carried out a detailed analysis of potential [C-H⋯O] and [C-H⋯F] interactions, though these undoubtedly will be playing a supporting role in the cooperative forces that constitute the "adhesive" within this complex multicomponent molecule.
61. - anions trapped within crystalline supermolecules made up of crown ethers as receptors for organic cations containing one or two secondary dialkylammonium centers. See for example: Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2068-2070.
62. The characteristics of the mass spectra of catenanes were first described by: Vetter, W.; Schill, G. Tetrahedron 1967, 23, 3079-3093.
63. c.
64. 6 were too complex to afford kinetic data.
65. (a) A similar process has been observed previously in a related [2]-catenane in which the same cyclophane and DN38C10 are the two components. See: Ashton, P. R.; Brown, C. L.; Chrystal, E. J. T.; Goodnow, T. T.; Kaifer, A. E.; Parry, K. P.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 634-639.
66. For a detailed kinetic analysis of the dynamic processes occurring in a related [3]catenane, see: (b) Ashton, P. R.; Boyd, S. E.; Claessens, C. G.; Gillard, R. E.; Menzer, S.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1997, 3, 788-798.
67. 6 are broadened by additional, unidentified, exchange processes. Resonances assignable to these nuclei are, however, resolved above room temperature as these processes enter the fast exchange regime (400 MHz).
68. Ballardini, R.; Balzani, V.; Brown, C. L.; Credi, A.; Gillard, R. E.; Montalti, M.; Philp, D.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, B. J.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 12503-12513.
69. Two distinct oxidation processes have also been observed for the 1/5DN38C10 macrocyclic polyether, which contains two DMN-type units, see: Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Hamers, C.; Mattersteig, G.; Montaiti, 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. Engl. 1998, 37, 333-337.