New supramolecular packing motifs: π-stacked rods encased in triply-helical hydrogen bonded amide strands

Abstract

The structure of N,N′,N″-tris(2-methoxyethyl)benzene-1,3,5-tricarboxamide consists of aryl rings self-assembled using a novel conjunction of organizational motifs into a π-stack surrounded by a triple helical network of hydrogen bonds, in a manner suggestive of a new mode of organization for some columnar liquid crystals.

References

1. G. R. Desiraju, Chem. Commun., 1997, 1475; G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311; C. B. Aakeröy, Acta Crystallogr., Sect. B., 1997, 53, 569; D. Braga and F. Grepioni, Coord. Chem. Rev., 1999, 183, 19.
2. X. Zhao, Y.-L. Change, F. W. Fowler and J. W. Lauher, J. Am. Chem. Soc., 1990, 112, 6627; F. Garcia-Tellado, S. J. Geib, S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 1991, 113, 9265; M. J. Krische, J.-M. Lehn, N. Kyritsakas and J. Fischer, Helv. Chim. Acta, 1998, 81, 1909; J. J. Wolff, F. Gredel, T. Oeser, H. Irngartinger and H. Pritzkow, Chem. Eur. J., 1999, 5, 29.
3. J.-M. Lehn, M. Maskal, A. DeCian and J. Fischer, J. Chem. Soc., Perkin Trans. 2, 1992, 461; M. W. Hosseini, R. Ruppert, P. Schaeffer, A. DeCian, N. Kyritskas and J. Fischer, Chem. Commun., 1994, 2135; R. Macías, N. P. Rath and L. Barton, J. Organomet. Chem., 1999, 581, 39; J. C. MacDonald and G. M. Whitesides, Chem. Rev., 1994, 94, 2383.
4. M. R. Ghadini, J. R. Granja, R. A. Milligan, D. E. McRee and N. Khazanovich, Nature, 1993, 366, 324.
5. I. S. Choi, X. Li, E. E. Simanek, R. Akaba and G. M. Whitesides, Chem. Mater., 1999, 11, 684.
6. S. Subramanian and M. J. Zaworotko, Coord. Chem. Rev., 1994, 137, 357.
7. E. Fan, J. Yang, S. J. Geib, T. C. Stoner, M. D. Hopkins and A. D. Hamilton, J. Chem. Soc., Chem. Commun., 1995, 1251.
8. P. Hobza, H. L. Selze and E. W. Schlag, J. Am. Chem. Soc., 1994, 116, 3500.
9. S. Chandrasekhar and G. S. Ranganath, Rep. Prog. Phys., 1990, 53, 57.
10. A. R. A. Palmans, J. A. J. M. Vekemans, H. Fischer, R. A. Hikmet and E. W. Meijer, Chem. Eur. J., 1997, 3, 300.
11. Y. Matsanuga, N. Miyajima, Y. Nakayasu, S. Saki and M. Yonega, Bull. Chem. Soc. Jpn., 1988, 61, 207.
12. K. Hanabusa, C. Koto, M. Kimura, H. Shirai and A. Kakehi, Chem. Lett., 1997, 429.
13. B. König, O. Möller, P. Bubenitschek and P. G. Jones, J. Org. Chem., 1995, 60, 4291.