Functionalization of the cyclodextrin platform with tetrathiafulvalene units: an efficient access towards redox active Langmuir–Blodgett films

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Yvan Le Bras, Marc Sallé, Philippe Leriche, Christophe Mingotaud, Pascal Richomme and Jørgen Møller


Abstract

Electroactive cyclodextrins persubstituted with pendant tetrathiafulvalene moieties were synthesized and electrochemically characterized by cyclic voltammetry. They show a very good ability to be transferred as Langmuir–Blodgett films, independently of the hydrophobic character of the redox active part.


References

  1. M. R. Bryce, J. Mater. Chem., 1995, 5, 1481 RSC and references cited therein.
  2. (a) L. M. Goldenberg, V. Y. Khodorkovsky, J. Y. Becker, P. J. Lukes, M. R. Bryce, M. C. Petty and J. Yarwood, Chem. Mater., 1994, 6, 1426 CrossRef CAS and references cited; (b) M. R. Bryce and M. C. Petty, Nature, 1995, 374, 771 CrossRef CAS; (c) L. M. Goldenberg, J. Y. Becker, O. Paz-Tal Levi, V. Y. Khodorkovsky, M. R. Bryce and M. C. Petty, J. Chem. Soc., Chem. Commun., 1995, 475 RSC; (d) P. Delhaès and V. M. Yartsev, Spectroscopy of New Materials, John Wiley and Sons, New York 1993, pp. 199–289 Search PubMed; (e) V. Morisson, C. Mingotaud, B. Agricole, M. Sallé, A. Gorgues, C. Garrigou-Lagrange and P. Delhaès, J. Mater. Chem., 1995, 5, 1617 RSC and references cited; (f) R. P. Pang, J. D. Wilkinson, M. C. Petty, C. Pearson and T. G. Ryan, J. Mater. Chem., 1995, 5, 1609 RSC.
  3. (a) Y. Kawabata, M. Matsumoto, M. Tanaka, H. Takahashi, Y. Iranitsu, S. Tamura, W. Tagaki, H. Nakahara and K. Fukuda, Chem. Lett., 1986, 1933 CAS; (b) Y. Kawabata, M. Matsumoto, T. Nakamura, M. Tanaka, E. Manda, H. Takahashi, S. Tamura, W. Tagaki, H. Nakahara and K. Fukuda, Thin Solid Films, 1988, 159, 353 CrossRef CAS; (c) P. Zhang, H. Parrot-Lopez, P. Tchoreloff, A. Baszkin, C. C. Ling, C. de Rango and A. W. Coleman, J. Phys. Org. Chem., 1992, 5, 518 CrossRef; (d) H. Parrot-Lopez, C. C. Ling, P. Zhang, A. Baszkin, G. Albrecht, C. de Rango and A. W. Coleman, J. Am. Chem. Soc., 1992, 114, 5479 CrossRef CAS; (e) M. H. Greenhall, P. Lukes, R. Kataky, N. E. Agbor, J. P. S. Badyal, J. Yarwood, D. Parker and M. C. Petty, Langmuir, 1995, 11, 3997 CrossRef CAS; (f) D. P. Parazak, A. R. Khan, V. T. D'Souza and K. J. Stine, Langmuir, 1996, 12, 4046 CrossRef CAS.
  4. (a) R. Breslow, Acc. Chem. Res., 1995, 28, 146 CrossRef CAS; (b) M. L. Bender and M. Komiyama, in Cyclodextrin Chemistry, Springer-Verlag, New York, 1978 Search PubMed.
  5. (a) G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803 CrossRef and references cited; (b) A. P. Croft and R. A. Bartsch, Tetrahedron, 1983, 39, 1417 CrossRef CAS and references cited; (c) F. Guillo, B. Hamelin, L. Jullien, J. Canceill, J.-M. Lehn, L. de Robertis and H. Driguez, Bull. Soc. Chim. Fr., 1995, 132, 857 CAS.
  6. (a) A. Gadelle and J. Defaye, Angew. Chem., Int. Ed. Engl., 1991, 30, 78 CrossRef; (b) H. H. Baer, A. Vargas Berenguel, Y. Y. Shu, J. Defaye, A. Gadelle and F. Santoyo Gonzales, Carbohydr. Res., 1992, 228, 307 CrossRef CAS.
  7. (a) J. Lau, O. Simonsen and J. Becher, Synthesis, 1995, 521 CrossRef CAS; (b) K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, P. Mørk, G. J. Kristensen and J. Becher, Synthesis, 1996, 407 CrossRef CAS.
  8. Bun4NPF6(0.1 mol dm–3), 100 mVs–1, 20 °C, Ar atmosphere.
  9. (a) P. Blanchard, N. Svenstrup and J. Becher, Chem. Commun., 1996, 615 RSC; (b) M. Jorgensen, K. A. Lerstrup and K. Bechgaard, J. Org. Chem., 1991, 56, 5684 CrossRef.
  10. E. Dupart, B. Agricole, S. Ravaine, C. Mingotaud, O. Fichet, P. Delhaès, H. Ohnuki, G. Munger and R. M. Leblanc, Thin Solid Films, 1994, 242, 575 CrossRef CAS.
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