A metallo-supramolecular double-helix containing a major and a minor groove

Chemical Communications

Volumn , Issue 20, 1999, Pages 2023-2024

  Hannon, Michael J ^a   Painting, Claire L ^a   Alcock, Nathaniel W ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; METAL ION;

ARCHITECTURE; ARTICLE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; TEMPERATURE;

EID: 0033592649     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905795a     Document Type: Article

References (20)

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2. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
3. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
4. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
5. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
6. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
7. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
8. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
9. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1155; E. C. Constable, Prog. Inorg. Chem., 1994, 42, 67; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft and T. Kulke, Chem. Eur. J., 1999, 5, 1862; C. Piguet, G. Bernardinelli and G. Hopfgartner, Chem. Rev., 1997, 97, 2005; R. W. Saalfrank and I. Bernt, Curr. Opin. Solid State Mater. Sci., 1998, 3, 407; A. F. Williams, Pure Appl. Chem., 1996, 68, 1285; J. S. Fleming, K. L. V. Mann, S. M. Couchman, J. C. Jeffery, J. A. McCleverty and M. D. Ward, J. Chem. Soc., Dalton Trans., 1998, 2047; M. Albrecht and R. Frohlich, J. Am. Chem. Soc., 1997, 119, 1656 and references therein.
10. M. J. Hannon, S. Bunce, A. J. Clarke and N. W. Alcock, Angew. Chem., Int. Ed., 1998, 38, 1277
11. M. J. Hannon, C. L. Painting, A. Jackson, J. Hamblin and W. Errington, Chem. Commun., 1997, 1807.
12. For examples of such interactions, see E.-I. Kim, S. Paliwal and C. S. Wilcox, J. Am. Chem. Soc., 1998, 120, 11 192; Y. Umezawa, S. Tsuboyama, K. Honda, J. Uzawa and M. Nishio, Bull. Chem. Soc. Jpn., 1998, 71, 1207; M. Nishio, Y. Umezawa, M. Hirota and Y. Takeuchi, Tetrahedron, 1995, 51, 8665; C. A. Hunter, Chem. Soc. Rev., 1994, 23, 101 and references therein.
13. For examples of such interactions, see E.-I. Kim, S. Paliwal and C. S. Wilcox, J. Am. Chem. Soc., 1998, 120, 11 192; Y. Umezawa, S. Tsuboyama, K. Honda, J. Uzawa and M. Nishio, Bull. Chem. Soc. Jpn., 1998, 71, 1207; M. Nishio, Y. Umezawa, M. Hirota and Y. Takeuchi, Tetrahedron, 1995, 51, 8665; C. A. Hunter, Chem. Soc. Rev., 1994, 23, 101 and references therein.
14. For examples of such interactions, see E.-I. Kim, S. Paliwal and C. S. Wilcox, J. Am. Chem. Soc., 1998, 120, 11 192; Y. Umezawa, S. Tsuboyama, K. Honda, J. Uzawa and M. Nishio, Bull. Chem. Soc. Jpn., 1998, 71, 1207; M. Nishio, Y. Umezawa, M. Hirota and Y. Takeuchi, Tetrahedron, 1995, 51, 8665; C. A. Hunter, Chem. Soc. Rev., 1994, 23, 101 and references therein.
15. For examples of such interactions, see E.-I. Kim, S. Paliwal and C. S. Wilcox, J. Am. Chem. Soc., 1998, 120, 11 192; Y. Umezawa, S. Tsuboyama, K. Honda, J. Uzawa and M. Nishio, Bull. Chem. Soc. Jpn., 1998, 71, 1207; M. Nishio, Y. Umezawa, M. Hirota and Y. Takeuchi, Tetrahedron, 1995, 51, 8665; C. A. Hunter, Chem. Soc. Rev., 1994, 23, 101 and references therein.
16. 2 meso).
17. int, = 0.0539). T = 180(2) K. Absorption correction by ψ-scans; minimum and maximum transmission factors: 0.73; 0.93. The lattice contains three fully occupied (as shown by test refinement) but highly mobile benzene molecules and one acetonitrile molecule (50% occupancy). Goodness-of-fit was 0.997, R1 [for 5837 reflections with I> 2σ(I)] = 0.0744, wR2 = 0.2093. Refinement used SHELXTL (G. M. Sheldrick, 1997). CCDC 182/1403. See http: //www.rsc.org/suppdata/cc/1999/2023/ for crystallographic files in .cif format.
18. Such meso- and rac-systems have also been observed by other workers. See, for example: A. Bilyk, M. M. Harding, P. Turner and T. W. Hambley, J. Chem. Soc., Dalton Trans., 1994, 2783; C. O. Dietrich-Buchecker, J. F. Nierengarten, J. P. Sauvage, N. Armaroli, V. Balzani and L. DeCola, J. Am. Chem. Soc., 1993, 115, 11 237.
19. Such meso- and rac-systems have also been observed by other workers. See, for example: A. Bilyk, M. M. Harding, P. Turner and T. W. Hambley, J. Chem. Soc., Dalton Trans., 1994, 2783; C. O. Dietrich-Buchecker, J. F. Nierengarten, J. P. Sauvage, N. Armaroli, V. Balzani and L. DeCola, J. Am. Chem. Soc., 1993, 115, 11 237.
20. The temperature range over which the resonances of the two isomers are distinct is insufficient for accurate determination of thermodynamic parameters. Simple modelling reveals that the box conformation cannot accommodate inter-strand π-stacking interactions. If maintained in solution, the face-edge π-stacking interactions may contribute to the enthalpic preference for the helix and the concomitant restrictions on the free rotation of the phenyl rings in the helix might contribute to the entropic preference for the meso-isomer.