Supramolecular Weaving

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 735-739

  Ashton, Peter R ^a   Collins, Andrew N ^b   Fyfe, Matthew C T ^a   Menzer, Stephan ^c   Fraser Stoddart, J ^a   Williams, David J ^c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Crystal engineering; Hydrogen bonds; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 0030754168     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707351     Document Type: Article

References (57)

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15. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
16. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
17. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
18. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
19. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
20. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
21. For recent examples of the noncovalent synthesis of polymeric supramolecular arrays utilizing hydrogen bonding, see a) J. A. Zerkowski, J. C. MacDonald, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 2382-2391; b) X. Wang, M. Simard, J. D, Wuest, ibid, 1994, 116, 12119-12120; S. Hanessian, M. Simard, S. Roelens, ibid. 1995, 117, 7630-7645; E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins, A. D. Hamilton, J. Chem. Soc. Chem. Commun. 1995, 1251-1252; e) K. E. Schwiebert, D. N. Chin, J. C. MacDonald, G. M. Whitesides, J. Am. Chem. Soc. 1996, 118, 4018-4029; f) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591; g) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. DeCian, J. Fischer, Tetrahedron Lett. 1996, 37, 1405-1408.
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42. 2CO/PhH at 20°C.
43. 2 = 0.3232 for 607 refined parameters. Computations for both of the structures were carried out on a SGI station with the SHELXTL package, version 5.03. The crystallographic data (excluding structure factors) for both of the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100088 Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: Int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
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45. -.
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53. See for example a) F. Takusagawa, T. F. Koetzle, Acta Crystallogr. Sect. B 1979, 35, 2888-2896; b) L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, ibid. 1991, 47, 776-782; c) H. Diaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545.
54. See for example a) F. Takusagawa, T. F. Koetzle, Acta Crystallogr. Sect. B 1979, 35, 2888-2896; b) L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, ibid. 1991, 47, 776-782; c) H. Diaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545.
55. See for example a) F. Takusagawa, T. F. Koetzle, Acta Crystallogr. Sect. B 1979, 35, 2888-2896; b) L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, ibid. 1991, 47, 776-782; c) H. Diaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545.
56. A. Zafar, J, Yang, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1996, 37, 2327-2330.
57. While this article was in press, we became aware of the research of Whang and Kim (D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451-452), who have combined hydrogen bonding and dative bonding interactions to generate interwoven supramolecular arrays.