Photochromic flavylium compounds as multistate/multifunction molecular-level systems

Abstract

Synthetic flavylium compounds can exist in several forms (multistate) that can be interconverted by more than one type of external stimulus (multifunctional). The intricate network of their reactions, when examined from the view point of ‘molecular-level devices’, reveals very interesting properties.

References

1. J.-M. LehnSupramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995.
2. Molecular Electronic Devices, ed. F. L. Carter, R. E. Siatkowsky and H. Woltjien, Elsevier, Amsterdam, 1988; K. E. Drexler, Nanosystems: Molecular Machinery, Manufacturing, and Computation, Wiley, New York, 1992; T. Thompson, Byte, 1996, 45.
3. D. Rouvray, Chem. Br., 1998, 34(2), 26.
4. V. Balzani and F. Scandola, Supramolecular Photochemistry, Ellis Horwood, Chichester, 1991.
5. L. B. Feringa, W. F. Jager and B. de Lange, Tetrahedron, 1993, 49, 8267.
6. A. P. de Silva and C. P. McCoy, Chem. Ind., 1994, 992.
7. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515.
8. V. Balzani and F. Scandola, in Comprehensive Supramolecular Chemistry, ed. D. N. Reinhoudt, Pergamon, Oxford, England, 1996, vol. 10, p. 687.
9. V. Balzani, A. Credi and F. Scandola, Chim. Ind. (Milan), 1997, 79, 751.
10. Photochromism—Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990.
11. For seminal examples concerning photochromic systems, see: (a) J. Daub, J. Salbeck, T. Knöchel, C. Fischer, H. Kunkely and K. M. Rapp, Angew Chem., Int. Ed. Engl., 1989, 28, 1494; (b) T. Iyoda, T. Saika, K. Honda and T. Shimidzu, Tetrahedron Lett., 1989, 30, 5429; (c) J. Daub, C. Fischer, J. Salbeck and K. Ulrich, Adv. Mater., 1990, 8, 366; (d) Y. Yokoyama, T. Ymamane and Y. Kurita, J. Chem. Soc., Chem. Commun., 1991, 1722; (e) K. Uchida and M. Irie, J. Am. Chem. Soc., 1993, 115, 6442; (f) M. Irie, Mol. Cryst. Liq. Cryst., 1993, 227, 263; (g) M. Irie, O. Miyatake, K. Uchida and T. Eriguchi, J. Am. Chem. Soc., 1994, 116, 9894; (h) M. J. Preigh, F.-T. Lin, K. Z. Ismail and S. G. Weber, J. Chem. Soc., Chem. Commun., 1995, 2091; (i) S. H. Kawai, S. L. Gilat, R. Posinet and J.-M. Lehn, Chem. Eur. J., 1995, 1, 285; (j) G. M. Tsivgoulis and J.-M. Lehn, Chem. Eur. J., 1996, 2, 1399; (k) M. Inouye, K. Akamatsu and H. Nakazumi, J. Am. Chem. Soc., 1997, 119, 9160.
12. For multiplexing optical systems based on mixtures of photochromic compounds, see: G. M. Tsivgoulis and J.-M. Lehn, Adv. Mater., 1991, 9, 627.
13. R. Brouillard, in The Flavonoids, Advances in Research, ed. J. Harborne, Chapman and Hall, London, 1988, p. 525; R. Brouillard, in Anthocyanins as food colors, ed. P. Markakis, Academic Press, New York, 1982, ch. 1.
14. R. Brouillard and J. E. Dubois, J. Am. Chem. Soc., 1997, 99, 1359.
15. R. Brouillard and J. Delaporte, J. Am. Chem. Soc., 1997, 99, 8461.
16. R. A. McClelland and S. Gedge, J. Am. Chem. Soc., 1980, 102, 5838.
17. R. A. McClelland and G. H. McGall, J. Org. Chem., 1982, 47, 3730.
18. F. Pina, M. J. Melo, L. Flamigni, R. Ballardini and M. Maestri, New. J. Chem., 1997, 21, 969.
19. F. Pina, M. J. Melo, M. Maestri, R. Ballardini and V. Balzani, J. Am. Chem. Soc., 1997, 119, 5556.
20. F. Pina, M. J. Melo, M. H. Santos, J. C. Lima, I. Abreu, R. Ballardini and M. Maestri, New J. Chem., 1998, in the press.
21. F. Pina, A. Roque, M. J. Melo, M. Maestri, L. Belladelli and V. Balzani, Chem. Eur. J., 1998, 4, 1184.
22. F. Pina, M. J. Melo, A. J. Parola, M. Maestri and V. Balzani, Chem. Eur. J., 1998, in the press.
23. F. Pina, J. Chem. Soc., Faraday Trans., 1998, 94, 2109.
24. C. Michaelis and R. Wizinger, Helv. Chim. Acta, 1951, 34, 1761; A. W. Johnson and R. R. Melhuish, J. Chem. Soc., 1947, 346; C. Bullow and H. Wagner, Ber. Dtsch. Chem. Ges., 1901, 34, 1782.
25. W. von Sperling, F. C. Werner and H. Kuhn, Ber. Bunsenges. Phys. Chem., 1966, 70, 530.
26. G. Haucke, P. Czerney, C. Igney and H. Hartmann, Ber. Bunsenges. Phys. Chem., 1989, 93, 805; G. Haucke, P. Czerney, D. Steen, W. Rettig and H. Hartmann, Ber. Bunsenges. Phys. Chem., 1993, 97, 561.
27. (a) P. Figueiredo, J. C. Lima, H. Santos, M.-C. Wigand, R. Brouillard and F. Pina, J. Am. Chem. Soc., 1994, 116, 1249; (b) F. Pina, L. Benedito, M. J. Melo, A. J. Parola and M. A. Bernardo, J. Chem. Soc. Faraday Trans., 1996, 92, 1693; (c) M. Maestri, R. Ballardini, F. Pina and M. J. Melo, J. Chem. Educ., 1997, 74, 1314.
28. R. Matsushima, H. Mizuno and H. Itoh, J. Photochem. Photobiol. A, 1995, 89, 251; R. Matsushima, H. Mizuno and A. Kajiura, Bull Chem. Soc. Jpn., 1994, 67, 1762; R. Matsushima and M. Suzuki, Bull Chem. Soc. Jpn., 1992, 65, 39.
29. J. Saltiel and Y.-P. Sun, in Photochromism-Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, ch. 3.
30. H. Eichenbaum, Science, 1997, 277, 330 For an example of an artificial system showing deep and shallow memory forms, see ref. 11(b).
31. A. P. de Silva, H. Q. N. Gunaratne and C. P. McCoy, Nature, 1993, 364, 42.
32. A. Credi, V. Balzani, S. J. Langford and J. F. Stoddart, J. Am. Chem. Soc., 1997, 119, 2679.
33. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, M. Montalti, N. Spencer, J. F. Stoddart and M. Venturi, Chem. Eur. J., 1997, 3, 1992.
34. P. Ball and L. Garvin, Nature, 1992, 355, 761; D. Bradley, Science, 1993, 259, 890.