From molecular ribbons to a molecular fabric

Chemistry - A European Journal

Volumn 5, Issue 1, 1999, Pages 381-384

  Mascal, Mark ^a   Hansen, Jens ^a   Fallon, Philip S ^a   Blake, Alexander J ^a   Heywood, Brigid R ^b   Moore, Madeleine H ^c   Turkenburg, Johan P ^c  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF SALFORD   (United Kingdom)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Crystal engineering; Hydrogen bonds; Ion pairs; Self assembly; Solid state structures

Indexed keywords

2,4,6 TRIAMINOPYRIMIDINE DERIVATIVE; AMMONIUM CARBONATE; AMMONIUM DERIVATIVE; CARBOXYALKYL 1,3,5 TRIAZINE 2,4,6 TRIONE DERIVATIVE; HYDROGEN; PYRIMIDINE DERIVATIVE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL; HYDROGEN BOND; MOLECULAR INTERACTION; STRUCTURE ANALYSIS;

EID: 0032901860     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990104)5:1<381::AID-CHEM381>3.0.CO;2-T     Document Type: Article

References (22)

1. Review: G. R. Desiraju, Chem. Commun. 1997, 1475, and references therein.
2. J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479.
3. J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025.
4. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
5. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
6. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
7. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
8. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
9. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
10. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
11. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
12. For some examples of how various research groups have made use of the hydrogen-bonding ribbon motif, see: a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117; b) H. Koyano, P. Bissel, Y. Yoshihara, K. Ariga, T. Kunitake, Chem. Eur. J. 1997, 3, 1077; W. T. S. Huck, R. Hulst, P. Timmerman, F. C. J. M. van Veggel, D. N. Reinhoudt, Angew. Chem. 1997, 109, 1046; Angew. Chem. Int. Ed. Engl. 1997, 36, 1006; d) Y. Ren, B. Zhao, X. Chai, A. Lu, S. Chen, Y. Cao, W. Yang, R. Lu, J. Duo, Y. Jiang, T. Li, Thin Solid Films 1997, 293, 170; e) T. M. Bohanon, S. Denziner, R. Fink, W. Paulus, H. Ringsdorf, M. Weck, Angew. Chem. 1995, 107, 102; Angew. Chem. Int. Ed. Engl. 1995, 34, 58; f) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37; g) K. Hanabusa, Y. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382.
13. J. A. Zerkowski, J. C. MacDonald, G. M. Whitesides, Chem. Mater. 1994, 6, 1250.
14. The application of hydrogen bonding to the generation of other two-dimensional assemblies has been reviewed: D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229.
15. D. A. Dunnigan, W. J. Close, J. Am. Chem. Soc. 1953, 75, 3615; W. J. Close, J. Am. Chem. Soc. 1953, 75, 3617; P. B. Russell, G. H. Hitchings, J. Am. Chem. Soc. 1952, 74, 3443.
16. D. A. Dunnigan, W. J. Close, J. Am. Chem. Soc. 1953, 75, 3615; W. J. Close, J. Am. Chem. Soc. 1953, 75, 3617; P. B. Russell, G. H. Hitchings, J. Am. Chem. Soc. 1952, 74, 3443.
17. D. A. Dunnigan, W. J. Close, J. Am. Chem. Soc. 1953, 75, 3615; W. J. Close, J. Am. Chem. Soc. 1953, 75, 3617; P. B. Russell, G. H. Hitchings, J. Am. Chem. Soc. 1952, 74, 3443.
18. M. Mascal, P. S. Fallon, A. S. Batsanov, B. R. Heywood, S. Champ, M. Colclough, J. Chem. Soc. Chem. Commun. 1995, 805.
19. C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 6409.
20. H ⋯ O distances <2.0 Å, X - H⋯ O angles > 170°.
21. The low incidence of trifurcated C=O hydrogen-bond acceptors has been determined by use of the Cambridge Structural Database: C. M. Bird, PhD Thesis, University of Cambridge, 1995.
22. The Cambridge Structural Database: F. H. Allen, O. Kennard, Chemical Design Automation News 1993, 8, 31.