Anion-Orchestrated Formation in the Crystalline State of [2]Pseudorotaxane Arrays

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1917-1920

  Ashton, Peter R ^b   Cantrill, Stuart J ^a   Preece, Jon A ^b   Stoddart, J Fraser ^a   Wang, Zhen He ^a   White, Andrew J P ^c   Williams, David J ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001365612     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991089k     Document Type: Article

References (42)

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24. Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Clink, P. T.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865-1869.
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27. (a) Ashton, P. R.; Baxter, I.; Cantrill, S. J.; Fyfe, M. C. T.; Glink, P. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem. Int. Ed. 1998, 37, 1294-1297.
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30. Ashton, P. R.; Bartsch, R. A.; Cantrill, S. J.; Hanes, R. E., Jr.; Hickingbottom, S. K.; Lowe, J. N.; Preece, J. A.; Stoddart, J. F.; Talanov V. S.; Wang, Z.-H. Tetrahedron Lett. 1999, 40, 3661-3664.
31. o|), 20 ≤ 115°] and 2264 parameters. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 132801. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB12 1EZ, U.K. (fax: (+44)1223-336-033. e-mail: teched@ccdc.cam.ac.uk).
32. Whereas the term "conformation" refers to the spatial arrangement of atoms in a single molecular species resulting from torsions about singl or partial double bonds, the term "co-conformation" has been utilized to describe the relative three-dimensional dispositions of (a) the constituent parts (e.g., host and guest) in supramolecular systems and of (b) the components of interlocked molecular compounds, such as catenanes and rotaxanes. See: Fyfe, M. C. T.; Clink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2068-2070.
33. Cantrill, S. J.; Preece, J. A.; Stoddart, J. F.; Wang, Z.-H.; White A. J. P.; Williams, D. J. Unpublished results. The X-ray crystal structure of TB24C8·2MeCN has been described in the literature recently. See: Bryan, J. C.; Sachleben, R. A.; Hay, B. P. Inorg. Chim. Acta 1999, 290, 86-94. For a description of the solid-state structure of TB24C8, also solved by us, see: Bryan, J. C.; Bunick, G. J.; Sachleben, R. A. Acta Crystallogr. 1999, C55, 250-252.
34. Cantrill, S. J.; Preece, J. A.; Stoddart, J. F.; Wang, Z.-H.; White A. J. P.; Williams, D. J. Unpublished results. The X-ray crystal structure of TB24C8·2MeCN has been described in the literature recently. See: Bryan, J. C.; Sachleben, R. A.; Hay, B. P. Inorg. Chim. Acta 1999, 290, 86-94. For a description of the solid-state structure of TB24C8, also solved by us, see: Bryan, J. C.; Bunick, G. J.; Sachleben, R. A. Acta Crystallogr. 1999, C55, 250-252.
35. Cantrill, S. J.; Preece, J. A.; Stoddart, J. F.; Wang, Z.-H.; White A. J. P.; Williams, D. J. Unpublished results. The X-ray crystal structure of TB24C8·2MeCN has been described in the literature recently. See: Bryan, J. C.; Sachleben, R. A.; Hay, B. P. Inorg. Chim. Acta 1999, 290, 86-94. For a description of the solid-state structure of TB24C8, also solved by us, see: Bryan, J. C.; Bunick, G. J.; Sachleben, R. A. Acta Crystallogr. 1999, C55, 250-252.
36. In our experience, if the [2]pseudorotaxane is a major solution-state component in such an equilibrium process, this observation is usually reflected in the LSI-MS with the base peak of the spectrum arising from the 1:1 complex and the free components giving rise to much less intense peaks. Conversely, if threading in solution is negligible, a peak arising from the 1:1 association of the two components is often observed in the mass spectrum. However, this signal may arise as a consequence of face-to-face complexation rather than of a threaded geometry and its intensity is usually less than that observed for the signals arising from the free components. See: Ashton, P. R.; Baxter, I.; Fyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297-2307.
37. (a) Ashton, P. R.; Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 12514-12524.
38. (b) Ashton, P. R.; Fyfe, M. C. T.; Hickingbottom, S. K.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1998, 4, 577-589.
39. (c) Ashton, P. R.; Fyfe, M. C. T.; Martínez-Díaz, M.-V.; Menzer, S.; Schiavo, C.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1998, 4, 1523-1534.
40. (d) Fyfe, M. C. T.; Stoddart, J. F.; Williams, D. J. Struct. Chem. 1999, 10, 243-259.
41. - anions in [C-H⋯F] hydrogen bonding and its importance in the solid state, see: Grepioni, F.; Cojazzi, G.; Draper, S. M.; Scully, N.; Braga, D. Organometallics 1998, 17, 296-307.
42. Crystallization has also been used to advantage in a high-yielding preparation of a [3]rotaxane following a reversible oxidative coupling of the thiol groups of two [2]pseudorotaxane supermolecules by a so-called molecular riveting action. See: Kolchinski, A. G.; Alcock, N. W.; Roesner, R. A.; Busch, D. H. Chem. Commun. 1998, 1437-1438.