View PDF Version
 
DOI: 10.1039/A702797D (Paper) Reference Section for: J. Mater. Chem., 1997, 7, 2033-2037

Langmuir–Blodgett films of a tetrathiafulvalene derivative substituted with an azobenzene group

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

Leonid M. Goldenberg, Martin R. Bryce, Stefan Wegener, Michael C. Petty, John P. Cresswell, Igor K. Lednev, Ronald E. Hester and John N. Moore

Abstract

The new tetrathiafulvalene derivative1, functionalised with an azobenzene substituent, has been synthesised. Cyclic voltammetric and spectroelectrochemical studies in solution demonstrate the reversible formation of the radical cation of 1. UV–VIS spectroscopy suggests that there is a weak interaction between the TTF and azobenzene moieties in compound 1, and demonstrates that trans–cis isomerisation occurs upon photolysis of the azobenzene substituent. Semi-conducting LB films of 1 have been assembled without the need for added fatty acid: room temperature conductivity values of the films before and after doping with iodine vapour were σrt=10–3–10–5 S cm–1 and 2×10–2–10–3 S cm–1 , respectively. No change in the conductivity of the LB films was observed under irradiation.

References

  1. J. R. Ferraro and J. M. Williams, Introduction to Synthetic Electrical Conductors, Academic Press, London, 1987 Search PubMed.
  2. M. R. Bryce, Chem. Soc. Rev., 1991, 20, 355 RSC.
  3. A. E. Underhill, J. Mater. Chem., 1992, 2, 1 RSC.
  4. J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini and M.-H. Whangbo, Organic Superconductors (including Fullerenes)Prentice Hall, New Jersey, 1992 Search PubMed.
  5. J. Mater. Chem., Special Issue on Molecular Conductors, 1995, 5, 1469 Search PubMed.
  6. For a review of electronically conductive LB films see: M. R. Bryce and M. C. Petty, Nature, 1995, 374, 771 Search PubMed.
  7. J. Richard, M. Vandevyver, A. Barraud, J. P. Morand, R. Lapouyade, P. Delhaes, J. F. Jacquinot and M. Roulliay, J. Chem. Soc., Chem. Commun., 1988, 754 RSC.
  8. L. M. Goldenberg, R. Andreu, M. Savirón, A. J. Moore, J. Garín, M. R. Bryce and M. C. Petty, J. Mater. Chem., 1995, 5, 1593 RSC.
  9. A. S. Dhindsa, Y. P. Song, J. P. Badyal, M. R. Bryce, Y. M. Lvov, M. C. Petty and J. Yarwood, Chem. Mater., 1992, 4, 724 CrossRef CAS.
  10. L. M. Goldenberg, V. Yu. Khodorkovsky, J. Y. Becker, P. J. Lukes, M. R. Bryce, M. C. Petty and J. Yarwood, Chem. Mater., 1994, 6, 1426 CrossRef CAS.
  11. A. S. Batsanov, M. R. Bryce, J. N. Heaton, A. J. Moore, P. J. Skabara, J. A. K. Howard, E. Ortí, P. M. Viruela and R. Viruela, J. Mater. Chem., 1995, 5, 1689 RSC.
  12. L. M. Goldenberg, J. Y. Becker, O. Paz-Tal Levi, V. Yu. Khodorkovsky, M. R. Bryce and M. C. Petty, J. Chem. Soc., Chem. Commun., 1995, 475 RSC.
  13. L. M. Goldenberg, J. Y. Becker, O. Paz-Tal Levi, V. Yu. Khodorkovsky, L. M. Shapiro, M. R. Bryce, J. R. Cresswell and M. C. Petty, J. Mater. Chem., 1997, 7, 901 RSC.
  14. Y. Xiao, Z. Yao and D. Jin, Langmuir, 1994, 10, 1848 CrossRef CAS.
  15. R. P. Parg, J. D. Kilburn, M. C. Petty, C. Pearson and T. G. Ryan, J. Mater. Chem., 1995, 5, 1609 RSC.
  16. Z. F. Liu, B. H. Loo, K. Hashimoto and A. Fujishima, J. Electroanal. Chem., 1991, 297, 133 CrossRef CAS.
  17. Z. F. Liu, K. Hashimoto and A. Fujishima, Faraday Discuss., 1992, 94, 221 Search PubMed.
  18. H. Tochibana, T. Nakamura, M. Matsumoto, H. Komizu, E. Mauda, H. Niino, A. Yabe and Y. Kawabata, J. Am. Chem. Soc., 1989, 111, 3080 CrossRef CAS.
  19. For a review of organic switches based on azobenzene derivatives, see: F. Vögtle, Supramolecular Chemistry, Wiley, Chichester, 1991, ch. 7 Search PubMed.
  20. S.-A. Chen and C. S. Liao, Synth. Met., 1993, 57, 4950 CrossRef CAS.
  21. J. Garín, J. Orduna, S. Uriel, A. J. Moore, M. R. Bryce, S. Wegener, D. S. Yufit and J. A. K. Howard, Synthesis, 1994, 489 CrossRef CAS For an efficient synthesis of TTF see: A. J. Moore and M. R. Bryce, Synthesis, 1997, 407 Search PubMed.
  22. C. A. Panetta, J. Baghdadchi and R. Metzger, Mol. Cryst. Liq. Cryst., 1984, 107, 103 CAS.
  23. C. A. Jones, M. C. Petty, G. G. Roberts, G. Davies, J. Yarwood, N. M. Ratcliffe and J. W. Barton, Thin Solid Films, 1987, 155, 187 CrossRef CAS.
  24. Y. Fu, J. Ouyang and A. B. P. Lever, J. Phys. Chem., 1993, 97, 13753 CrossRef.
  25. L. M. Goldenberg, C. Pearson, M. R. Bryce and M. C. Petty, J. Mater. Chem., 1996, 6, 699 RSC.
  26. G. H. Cross, I. R. Girling, I. R. Peterson and N. A. Cade, Electrooptics Lett., 1986, 22, 1111 Search PubMed.
  27. J. B. Torrance, B. A. Scott, B. Welber, F. B. Kaufman and P. E. Seiden, Phys. Rev. B, 1979, 19, 730 CrossRef CAS.
  28. R. Dieing, V. Morisson, A. J. Moore, L. M. Goldenberg, M. R. Bryce, J.-M. Raoul, M. C. Petty, J. Garín, M. Savirón, I. K. Lednev, R. E. Hester and J. N. Moore, J. Chem. Soc., Perkin Trans. 2, 1996, 1587 RSC.
  29. J. Griffiths, Colour and Constitution of Organic Molecules, Academic Press, London, 1976 Search PubMed.
  30. H. Rau, in Photochromism. Molecules and Systems, ed. H. Durr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, ch. 4, p. 165 Search PubMed.
  31. It has been noted that the structure of multilayer films of amphiphilic metal(dmit)2 charge-transfer salts (metal – Ni, Pd, Pt) depends upon the time that the floating film is left on the subphase surface befor compression. S. K. Gupta, D. M. Taylor, P. Dynarowicz, E. Barlow, C. E. A. Wainwright and A. E. Underhill, Langmuir, 1992, 8, 3057 Search PubMed; C. Pearson, A. S. Dhindsa, L. M. Goldenberg, R. A. Singh, R. Dieing, A. J. Moore, M. R. Bryce and M. C. Petty, J. Mater. Chem., 1995, 5, 1601 CrossRef CAS However, this is not usually observed with TTF derivatives.
  32. A. S. Dhindsa, J. P. Badyal, M. R. Bryce, M. C. Petty, A. J. Moore and Y. M. Lvov, J. Chem. Soc., Chem. Commun., 1990, 970 RSC.
  33. B. Tieke, Adv. Mater., 1991, 2, 222 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.