Supramolecular mesomorphic structures based on 2,5-dialkoxyterephthalicacid derivatives

Abstract

Self-assembly of 2,5-di-n-alkoxyterephthalic acids (C_nOTpA) and 2,5-di-n-hexylterephthalic acid (C₆TpA) as bifunctional hydrogen bond donors with bifunctional acceptors 1,3-diaminopropane (Dap), piperazine (Pip) and 4,4′-bipyridine (Bipy) has been investigated, both in the crystal lattice and in the mesophase. Stoichiometric mixtures of compounds C_nOTpA with diamine Dap form mesophases with a lamellar-type structure and constitute, to the best of our knowledge, the first examples of the generation of mesophases from 2,5-di-n-alkoxyterephthalic acids and bifunctional diamines. The liquid crystalline behaviour of these mixtures was characterized using X-ray scattering, DSC and polarizing microscopy. The self-assembly of complexes C₆TpA·Bipy and C₆TpA·Pip in the crystal lattice was characterized using single crystal X-ray structural analysis. In the crystal lattice of C₆TpA·Bipy, only hydrogen bonding interactions between the neutral acid and the base were observed. However, in the crystal structure of cocrystals of C₆TpA with Pip, an ionic interaction was observed due to proton transfer from the acid group to the basic nitrogen atoms of the base.

References

1. (a) D. Philp and J. F. Stoddart, Angew. Chem., 1996, 108, 1242; Angew. Chem., Int. Ed. Engl., 1996, 35, 1154; (b) J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995; (c) G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 1991, 254, 1312; (d) J. S. Lindsey, New J. Chem., 1991, 15, 153; (e) D. S. Lawrence, T. Jiang and M. Levett, Chem. Rev., 1995, 95, 2229; (f) J. Fredericks, J. Yang, S. J. Geib and A. D. Hamilton, Proc. Ind. Acad. Sci. (Chem. Sci.), 1994, 106, 923; (g) A. D. Burrows, C.-W. Chan, M. M. Chowdhry, J. E. McGrady and D. M. P. Mingos, Chem. Soc. Rev., 1995, 24, 329; (h) A. R. J. Sellens, P. J. I. Runciman, A. C. Griffin and E. S. Bryant, Mol. Cryst. Liq. Cryst., 1989, 166, 123.
2. C. M. Paleos and D. Tsiourvas, Angew. Chem., 1995, 107, 1839; Angew. Chem., Int. Ed. Engl., 1995, 34, 1696.
3. C. G. Bazuin and A. Tork, Macromolecules, 1995, 28, 8877.
4. H. Ringsdorf, R. Wüstefeld, E. Zerta, M. Ebert and J. H. Wendorff, Angew. Chem., 1989, 101, 934; Angew. Chem., Int. Ed. Engl., 1989, 28, 914.
5. A. Liebmann, C. Mertesdorf, T. Plesnivy, H. Ringsdorf and J. H. Wendorff, Angew. Chem., 1991, 103, 1358; Angew. Chem., Int. Ed. Engl., 1991, 30, 1375.
6. (a) T. Kato and J. M. J. Fréchet, J. Am. Chem. Soc., 1989, 111, 8533; (b) T. Kato, A. Fujishima and J. M. J. Fréchet, Chem. Lett., 1990, 919; (c) T. Kato, P. G. Wilson, A. Fujishima and J. M. J. Fréchet, Chem. Lett., 1990, 2003; (d) T. Kato, T. Uryu, F. Kaneuchi, C. Jin and J. M. J. Fréchet, Liq. Cryst., 1993, 14, 1311; (e) M. Fukumasa, T. Kato, T. Uryu and J. M. J. Fréchet, Chem. Lett., 1993, 65.
7. (a) L. Y. Yu, Liq. Cryst., 1993, 14, 1303; (b) H. Kihara, T. Kato, T. Uryu, S. Ujiie, U. Kumar, J. M. J. Fréchet, D. W. Bruce and D. J. Price, Liq. Cryst., 1996, 21, 25; (c) T. Kato, H. Kihara, T. Uryu, S. Ujiie, K. Iimura, J. M. J. Fréchet and U. Kumar, Ferroelectrics, 1993, 148, 161.
8. (a) T. Kato and J. M. J. Fréchet, Macromolecules, 1989, 22, 3818; (b) T. Kato, M. Nakano, T. Moteki, T. Uryu and S. Ujiie, Macromolecules, 1995, 28, 8875; (c) R. V. Tal'roze, S. A. Kuptsov, T. I. Sycheva, V. S. Bezborodov and N. A. Platé, Macromolecules, 1995, 28, 8689; (d) C. G. Bazuin and A. Tork, Macromolecules, 1995, 28, 8877.
9. (a) C. Fouquey, J.-M. Lehn and A.-M. Levelut, Adv. Mater., 1990, 2, 254; (b) J.-M. Lehn, M. Mascal, A. DeCian and J. Fischer, J. Chem. Soc., Chem. Commun., 1990, 479; (c) J.-M. Lehn, M. Mascal, A. DeCian and J. Fischer, J. Chem. Soc., Perkin Trans. 2, 1992, 461; (d) M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197; (e) M. W. Hosseini, G. Brand, P. Schaeffer, R. Ruppert, A. De Cian and J. Fischer, Tetrahedron Lett., 1996, 37, 1405; (f) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135.
10. (a) P. K. Bhowmik, X. Wang and H. Han, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 1995, 36(2), 124; (b) P. K. Bhowmik, X. Wang, H. Han and A. M. Sarker, 324; (c) H. Han, A. H. Molla and P. K. Bhowmik, 332.
11. (a) C. Alexander, C. P. Jariwala, C. M. Lee and A. C. Griffin, Macromol. Symp., 1994, 77, 283; (b) P. Bladon and A. C. Griffin, Macromolecules, 1993, 26, 6604.
12. J. J. Kane, R.-F. Liao, J. W. Lauher and F. W. Fowler, J. Am. Chem. Soc., 1995, 117, 12003.
13. The term ‘bifunctional’ implies that the self-assembling ‘monomer’ has two hydrogen bonding sites, which can be used to connect the molecule to two (complementary or self-complementary) units along a hydrogen-bonded chain.
14. V. Enkelmann, S. Valiyaveettil, G. Moessner and K. Müllen, Supramol. Sci., 1995, 2, 3.
15. M. H. P. van Genderen, M. Pfaadt, C. Möller, S. Valiyaveettil and H. W. Spiess, J. Am. Chem. Soc., 1996, 118, 3661; M. Pfaadt, G. Moessner, D. Pressner, S. Valiyaveettil, C. Boeffel, K. Müllen and H. W. Spiess, J. Mater. Chem., 1995, 5, 2265.
16. (a) K. Eichhorst-Gerner, A. Stabel, G. Moessner, D. Declerq, S. Valiyaveettil, V. Enkelmann, K. Müllen and J. P. Rabe, Angew. Chem., 1996, 108, 1599; Angew. Chem., Int. Ed. Engl., 1996, 35, 1492; (b) P. Vanoppen, P. C. M. Grim, M. Rücker, S. De Feyter, G. Moessner, S. Valiyaveettil, K. Müllen and F. C. De Schryver, J. Phys. Chem., 1996, 100(50), 19 636.
17. S. Valiyaveettil, G. Moessner, V. Enkelmann, C. Meiners, M. Pfaadt, H. W. Spiess and K. Müllen, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 1996, 37(2), 817.
18. H. Günzler and H. Böck, IR-Spektroskopie, Verlag Chemie, Weinheim, 1983, pp. 218–219.
19. M. Hesse, H. Meier and B. Zeeh, Spektroskopische Methoden in der Organischen Chemie, Georg Thieme Verlag, Stuttgart, 1987, p. 60; IR data in ref. 1h.
20. M. Ballauff and G. F. Schmidt, Makromol. Chem., Rapid Commun., 1987, 8, 93.
21. M. B. Steinbrunn and G. Wenz, Angew. Chem., 1996, 108, 2274; Angew. Chem., Int. Ed. Engl., 1996, 35, 2139; H. Rinke and E. Istel, Methoden der Org. Chem.(Houben-Weyl), 4th edn. Georg Thieme Verlag, Stuttgart, 1963, vol. 14(2), p. 99.
22. C. Meiners, S. Valiyaveettil and K. Müllen, unpublished results.
23. M. Etter, J. Phys. Chem., 1991, 95, 4606.
24. J. March, Advanced Organic Chemistry, 2nd edn., McGraw-Hill, New York, 1977, p. 228.
25. S. H. Pine, J. B. Hendrickson, D. J. Cram and G. S. Hammond, Organische Chemie, Vieweg, Braunschweig, 1987, p. 771.
26. M. Rehahn, A. D. Schlüter and W. J. Feast, Synthesis, 1988, 386.