Hydrogen bonded liquid crystals from nitrophenols and alkoxystilbazoles

(Note: The full text of this document is currently only available in the PDF Version )

Daniel J. Price, Kimberley Willis, Tim Richardson, Goran Ungar and Duncan W. Bruce


Abstract

Three series of hydrogen bonded adducts have been formed between 4-alkoxy-4′-stilbazoles and the nitrophenols 4-nitrophenol, 3-nitrophenol and 2,4-dinitrophenol. Each series is mesomorphic displaying both nematic and smectic A phases, in sharp contrast to the behaviour of the individual components. The binary phase behaviour of mixtures of 3-nitrophenol and 4-octyloxystilbazole is reported, and gives conclusive evidence for the formation of a one-to-one hydrogen bonded adduct. Electronic spectroscopy of 2,4-dinitrophenol/decyloxystilbazole was very informative and showed that the higher energy, ionic hydrogen bonded state, corresponding to proton transfer, was significantly populated through the mesophase, and that the mesophase provides an additional stabilisation for this state.


References

  1. D. Vorländer, Z. Phys. Chem., 1923, 105, 211 CAS; G. M. Bennett and B. Jones, J. Chem. Soc., 1939, 420 RSC.
  2. C. Eaborn, J. Chem. Soc., 1952, 2840 RSC; A. Polishchuk, T. V. Timofeeva, N. N. Makarova, M. Yu. Antipin and Yu. T. Struchov, Liq. Cryst., 1991, 9, 433 CAS.
  3. J. D. Bunning, J. E. Lydon, C. Eaborn, P. M. Jackson, J. W. Goodby and G. W. Gray, J. Chem. Soc., Faraday Trans. 1, 1982, 713 RSC.
  4. F. Henrich, S. Diele and C. Tschierske, Liq. Cryst., 1994, 17, 827 CAS.
  5. For reviews of this subject see: G. A. Jeffery and L. M. Wingert, Liq. Cryst., 1992, 12, 179 Search PubMed; G. A. Jeffery, Acc. Chem. Res., 1986, 19, 168 CrossRef.
  6. C. Paleos and D. Tsiourvas, Angew. Chem., Int. Ed. Engl., 1995, 34, 1696 CrossRef CAS.
  7. M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197 RSC; M.-J. Brienne, J. Gabard, J.-M. Lehn and I. Stibor, J. Chem. Soc., Chem. Commun., 1993, 420 RSC.
  8. L. J. Yu, J. M. Wu and S. L. Wu, Mol. Cryst. Liq. Cryst., 1991, 198, 407 CAS; L. J. Yu and J. L. Pan, Liq. Cryst., 1993, 14, 829 CAS; L. J. Yu, Liq. Cryst., 1993, 14, 1303 CAS.
  9. C. M. Lee, C. P. Jarwala and A. C. Griffin, Polymer, 1994, 35, 4550 CrossRef CAS.
  10. D. J. Price, PhD thesis, Sheffeld University, 1995; H. Kihara, T. Kato, T. Uryu, S. Ujiie, K. Iimura, U. Kumar, J. M. J. Fréchet, D. W. Bruce and D. J. Price, Liq. Cryst., 1996, 21, 25 Search PubMed; D. J. Price, H. Adams and D. W. Bruce, Mol. Cryst. Liq. Cryst., 1996, 289, 127 CAS; K. Willis, J. E. Luckhurst, D. J. Price, J. M. J. Fréchet, H. Kihara, T. Kato, G. Ungar and D. W. Bruce, Liq. Cryst., 1996, 21, 585 Search PubMed.
  11. T. Kato and J. M. J. Fréchet, J. Am. Chem. Soc., 1989, 111, 8533 CrossRef CAS; T. Kato and J. M. J. Fréchet, Macromolecules, 1989, 22, 3818 CrossRef CAS; U. Kumar, T. Kato and J. M. J. Fréchet, J. Am. Chem. Soc., 1992, 114, 6630 CrossRef CAS; T. Kato, H. Kihara, T. Uryu, A. Fuijishima and J. M. J. Fréchet, Macromolecules, 1992, 25, 6836 CrossRef CAS; T. Kato, H. Kihara, U. Kumar, T. Uryu and J. M. J. Fréchet, Angew. Chem., Int. Ed. Engl., 1994, 33, 1644 CrossRef; T. Kato, P. G. Wilson, A. Fuijishima and J. M. J. Fréchet, Chem. Lett., 1990, 2003 CAS; T. Kato, J. M. J. Fréchet, P. G. Wilson, T. Saito, T. Uryu, A. Fuijishima, C. Sin and F. Kaneuch, Chem. Mater., 1993, 5, 1094 CrossRef CAS; T. Kato, A. Fuijishima and J. M. J. Fréchet, Chem. Lett., 1990, 912; M. Fukumassa, T. Kato, T. Uryu and J. M. J. Fréchet, Chem. Lett., 1993, 65 CAS; T. Kato, H. Kihara, T. Uryu, S. Ujiie, K. Iimura, J. M. J. Fréchet and U. Kumar, Ferroelectrics, 1994, 148, 1303.
  12. D. W. Bruce and D. J. Price, Adv. Mater. Opt. Electron., 1994, 4, 273 CAS.
  13. H. Adams, D. W. Bruce, D. J. Price, G. Ungar and K. Willis, J. Mater. Chem., 1995, 5, 2195 RSC.
  14. D. W. Bruce, D. A. Dunmur, E. Lalinde, P. M. Maitlis and P. Styring, Liq. Cryst., 1988, 3, 385 CrossRef CAS.
  15. CRC Handbook of Chemistry and Physics, ed. D. R. Lide, 75th edn., CRC Press Inc., Boca Raton, Florida Search PubMed.
  16. R. Lindemann and G. Zundel, J. Chem. Soc., Faraday Trans. 2, 1972, 68, 979 RSC; R. Lindemann and G. Zundel, J. Chem. Soc., Faraday Trans. 2, 1977, 73, 788 RSC.
  17. D. J. Price, T. Richardson and D. W. Bruce, J. Chem. Soc., Chem. Commun., 1995, 1911 RSC.
  18. K. R. Seddon, personal communication, 1995.
  19. D. Hadzi, Pure Appl. Chem., 1965, 11, 435 CAS.
  20. D. W. Brown, A. J. Floyd and M. Sainsbury, Organic Spectroscopy, Wiley, Bath, 1988 Search PubMed.
  21. S. L. Johnson and K. A. Rumon, J. Phys. Chem., 1965, 69, 74 CrossRef CAS.
  22. T. Kato, personal communication.
Click here to see how this site uses Cookies. View our privacy policy here.