Improved template-directed synthesis of cyclobis(paraquat-p-phenylene)

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9591-9595

  Asakawa, Masumi ^a   Dehaen, Wim ^b   L'abbé, Gerrit ^b   Menzer, Stephan ^c   Nouwen, Jan ^b   Raymo, Françisco M ^a   Stoddart, J Fraser ^a   Williams, David J ^c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001573077     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961488i     Document Type: Article

References (47)

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27. For computational studies on cyclobis(paraquat-p-phenylene), see: (a) Ricketts, H. G.; Stoddart, J. F.; Hann, M. M. In Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwer: Dordrecht, 1994; pp 377-390. (b) Smit, E. A.; Libenthal, R. R.; Fonseca, R. J.; Smit, D. K. Anal. Chem. 1994, 66, 3013-3020. (c) Castro, R.; Berardi, M. J.; Córdova, E.; Ochoa de Olza, M.; Kaifer, A. E.; Evanseck, J. D. J. Am. Chem. Soc. 1996, 118, 10257-10268. (d) Castro, R.; Nixon, K. R.; Evanseck, J. D.; Kaifer, A. E. J. Org. Chem. 1996, 61, 7298-7303.
28. For computational studies on cyclobis(paraquat-p-phenylene), see: (a) Ricketts, H. G.; Stoddart, J. F.; Hann, M. M. In Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwer: Dordrecht, 1994; pp 377-390. (b) Smit, E. A.; Libenthal, R. R.; Fonseca, R. J.; Smit, D. K. Anal. Chem. 1994, 66, 3013-3020. (c) Castro, R.; Berardi, M. J.; Córdova, E.; Ochoa de Olza, M.; Kaifer, A. E.; Evanseck, J. D. J. Am. Chem. Soc. 1996, 118, 10257-10268. (d) Castro, R.; Nixon, K. R.; Evanseck, J. D.; Kaifer, A. E. J. Org. Chem. 1996, 61, 7298-7303.
29. For computational studies on cyclobis(paraquat-p-phenylene), see: (a) Ricketts, H. G.; Stoddart, J. F.; Hann, M. M. In Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwer: Dordrecht, 1994; pp 377-390. (b) Smit, E. A.; Libenthal, R. R.; Fonseca, R. J.; Smit, D. K. Anal. Chem. 1994, 66, 3013-3020. (c) Castro, R.; Berardi, M. J.; Córdova, E.; Ochoa de Olza, M.; Kaifer, A. E.; Evanseck, J. D. J. Am. Chem. Soc. 1996, 118, 10257-10268. (d) Castro, R.; Nixon, K. R.; Evanseck, J. D.; Kaifer, A. E. J. Org. Chem. 1996, 61, 7298-7303.
30. For computational studies on cyclobis(paraquat-p-phenylene), see: (a) Ricketts, H. G.; Stoddart, J. F.; Hann, M. M. In Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwer: Dordrecht, 1994; pp 377-390. (b) Smit, E. A.; Libenthal, R. R.; Fonseca, R. J.; Smit, D. K. Anal. Chem. 1994, 66, 3013-3020. (c) Castro, R.; Berardi, M. J.; Córdova, E.; Ochoa de Olza, M.; Kaifer, A. E.; Evanseck, J. D. J. Am. Chem. Soc. 1996, 118, 10257-10268. (d) Castro, R.; Nixon, K. R.; Evanseck, J. D.; Kaifer, A. E. J. Org. Chem. 1996, 61, 7298-7303.
31. (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
32. (b) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774.
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34. (a) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
35. (b) Desiraju, G. R. In The Crystal as a Supramolecular Entity, Desiraju, G. R., Ed. John Wiley & Sons: New York, 1996; pp 31-61.
36. Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701.
37. (a) Philp, D.; Stoddart, J. F. Synlett 1991, 445-448.
38. (b) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
39. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
40. For the synthesis of 1,5-bis(2-(2-hydroxyethoxy)ethoxy)naphthalene (6), see ref 1c.
41. Connors, K. A. Binding Constants; Wiley: New York, 1987.
42. 6, respectively). For the approximate coalescence treatment, see: Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
43. + ions arising from the 1:1 complex.
44. The mean interplanar separations between the "inside" 1,5-dioxynaphthalene residue and the "outside" and "inside" bipyridinium units are 3.32 and 3.37 Å, respectively, and the corresponding distance between the "outside" 1,5-dioxynaphthalene residue and the "inside" bipyridinium unit is 3.36 Å. Within the polar stacks between the "outside" 1,5-dioxynaphthalene residue and the "outside" bipyridinium unit, the mean interplanar separation is 3.32 Å.
45. α protons on the "inside" bipyridinium unit and the middle oxygen atom of the proximal polyether chains of both the "inside" and "outside" naphthalene-based threads. For the "inside" thread, the [C-H⋯O] hydrogen bonding geometries are [C⋯O], [H⋯O] distances, [C-H⋯O] angles: 3.30, 2.45 Å, 148°, and for the "outside" thread, 3.07, 2.39 Å, 127°, respectively.
46. The [H⋯π] distances associated with the [C-H⋯π] interactions are 2.57 Å and the associated [C-H⋯π] angles are 146°.
47. 2 under reduced pressure.