Abstract
The anils of salicylaldehyde comprise a chemical system which exhibits the properties of solid-state photochromism and thermochromism, and therefore are interesting for practical applications. In this paper the topochemical factors responsible for these properties are explored, together with the mechanism of the photochromic process and the nature of the colored anil molecule. For a better understanding of these problems the search incorporates solution and flash photolysis studies. Finally, new developments in which anils are used in different matrices like polymers, Langmuir-Blodgett films and cyclodextrins are reviewed, together with a number of potential applications.
Similar content being viewed by others
References
Senier, A. and Shepheard, F. G.:J. Chem. Soc. 95, 1943 (1909).
Senier, A., Shepheard, F. G., and Clarke, R.:J. Chem. Soc. 101, 1952 (1912).
Cohen, M. D. and Schmidt, G. M. J.:J. Chem. Phys. 66, 2442 (1962).
Cohen, M. D., Hirshberg, Y., and Schmidt, G. M. J.:J. Chem. Soc. 2051 (1964).
Cohen, M. D. and Flavian, S.:J. Chem. Soc. (B), 334 (1967).
Cohen, M. D.:J. Chem. Soc. (B) 373 (1968); Cohen, M. D. and Green, B. S.:Chem. Britain 9, 490 (1973).
Sacconi, L., Ciampolini, M., and Speroni, G. P.:J. Am. Chem. Soc. 87, 3102 (1965).
Chakravorty, A.:Inorg. Chem. 4, 127 (1965).
Bregman, J., Leiserowitz, L., and Osaki, K.:J. Chem. Soc. 2086 (1964); Bregman, J., Leiserowitz, L., and Schmidt, G. M. J.:J. Chem. Soc. 2068 (1964).
Bregman, J., Mond, E., and Schmidt, G. M. J.: unpublished data.
Schmidt, G. M. J.: unpublished data.
Ubbelohde, A. R. and Gallagher, K. J.:Acta Cryst. 8, 71 (1955).
Hadzi, D.:J. Chem. Soc. 2143 (1956).
Morgan, K. J.:J. Chem. Soc. 2151 (1961).
Schmidt, G. M. J.: inReactivity of the Photoexcited Organic Molecule, Interscience, London (1967), p. 227.
Burawoy, A., Salem A. G., and Thompson, A. R.:J. Chem. Soc. 4793 (1952).
Nakagaki, R., Kobayashi, T., Nakamura, J., and Nagakura, S.:Bull. Chem. Soc. Jpn. 50, 1909 (1977).
Hadjoudis, E., Vittorakis, M., and Moustakali-Mavridis, I.:Chemtronics 1, 58 (1986).
Zaitsev, B. E., Allenov, V. M., Golitsina, L. V., and Dokunikhin, N. S.:Zh. Fiz. Khim. 45(5), 1045 (1971).
Brown, P. S., Wallwork, S. C., and Wilson, A.:Acta Crvstal. 17, 168 (1964).
Cohen, M. D., Flavian, S., and Leiserowitz, L.:J. Chem. Soc. (B) 329 (1967).
Hadjoudis, E.:J. Photochem. 17, 355 (1981).
Fuson, R. C.:,J. Org. Chem. 8, 64 (1943).
Schonberg, A., Mustafa, A., and Asker, W.:J. Am. Chem. Soc. 76, 4134 (1954).
Sheppard, S. E. and Brigham, H. R.:J. Am. Chem. Soc. 66, 380 (1944).
Bartlett, P. D. and Seidel, B.:J. Am. Chem. Soc. 83, 581 (1961).
Gegiou, D. and Fischer, E.:Chem. Phys. Letters 10, 99 (1971).
Rosenfeld, T., Ottolenghi, M., and Meyer, A. Y.:Mol. Photochem. 5, 39 (1973).
Laverty, J. J. and Gardlund, Z. G.:Polymer Letters 7, 161 (1969).
Higelin, D. and Sixl, H.:Chem. Phys. 77, 391 (1983).
Cohen, M. D., Schmidt, G. M. J., and Flavian, S.:J. Chem. Soc. 2041 (1964).
Burr, A. A., Llewellyn, E. J., and Lothian, G. F.:Trans. Faraday Soc. 60, 2177 (1964).
Hockert, E. N. and Dickamer, H. G.:J. Chem. Phys. 67, 5178 (1977).
Dudek, G. O. and Dudek, E. P.:J. Am. Chem. Soc. 88, 2407 (1966).
Weller, A.:Z. Electrochem. 60, 1144 (1956); Weller, A.: inProgress in Reaction Kinetics, Vol. VI, Pergamon, London (1961), p. 188.
Ottolengi, M. and McClure, D. S.:J. Chem. Phys. 46, 4613 (1967).
Hadjoudis, E.:Mol. Cryst. Liq. Cryst. 13, 233 (1971).
Arcovito, G., Bonamico, M., Domenicano, A., and Vaciago, A.:J. Chem. Soc. (B) 733 (1969).
Cohen, M. D.:Pure Appl. Chem. 9, 567 (1964).
Burr, A. H. and Hobson, A. D.:Acta Cryst. B25, 2662 (1978).
Destro, R., Gavezzotti, A., and Simonetta, M.:Acta Crystal. B34, 2867 (1978).
Inabe, T., Gautier-Luneau, I., Hoshino, N., Okaniwa, K., Okamoto, H., Mitani, T., Nagashima, U., and Maruyama, Y.:Bull. Chem. Soc. Jpn. 64, 801 (1991).
Hadjoudis, E., Moustakali-Mavridis, I., and Xexakis, J.:Isr. J. Chem. 18, 202 (1979).
Hadjoudis, E., Vittorakis, M., and Moustakali-Mavridis, I.:Mol. Cryst. Liq. Cryst. 137, 1 (1986).
Hadjoudis, E. and co-workers: unpublished data (1992).
Hadjoudis, E.: inPhotochromism Molecules and Systems, Durr, H. and Bouas-Laurent, H., Eds., Elsevier, Amsterdam (1990), p. 685.
Kawato, T., Koyama, H., Kanotomi, H., and Isshiki, M.:J. Photochem. 28, 103 (1985).
Moustakali-Mavridis, I., Hadjoudis, E., and Mavridis, A.:Acta Crystal. B34, 3709 (1978).
Moustakali-Mavridis, I., Hadjoudis, E., and Mavridis, A.:Acta Crystal. B36, 1126 (1980).
Moloney, G. P., Gable, R. W., Iskander, M. N., Craik, D. J., and Mackay, M. F.:Aust. J. Chem. 43, 99 (1990).
Hadjoudis, E., Milia, F., Seliger, J., Zagar, V., and Blinc, R.:Chem. Phys. 156, 149 (1991).
Hadjoudis, E., Vittorakis, M., and Moustakali-Mavridis, I.:Tetrahedron 43, 1345 (1987).
Inabe, T.:New J. Chem. 15, 129 (1991).
Wettermark, G. and Dogliotti, L.:J. Am. Phys. 40, 1486 (1964).
Becker, R. S. and Richey, W. F.:J. Amer. Chem. Soc. 89, 1298 (1967).
Margerum, J. D. and Sousa, J.A.:Appl. Spectrosc. 19, 91 (1965).
Ledbetter, J. W., Jr.:J. Phys. Chem. 70, 2245 (1966).
Margerum, J. D. and Miller, L. J.: inPhotochromism, Brown, G. H., Ed., Wiley-Interscience, New York (1971), p. 557.
Simonava, A. P., Nurmukhametov, R. N., and Prokhoda, A. L.:Dokl. Phys. Chem. 230, 936 (1976).
Nurmukhametov, R. N., Betin, O. I., and Shigorin, D. N.:Dokl. Phys. Chem. 230, 828 (1976).
Grellmann, K. H. and Tauer, E.:Tetrahedron Lett. 3707 (1974).
Ledbetter, J. W.:J. Phys. Chem. 81, 54 (1977).
Csaszar, J., Balog, J., and Makary, A.:Acta Chim. (Budapest) 473 (1978).
Seliskar, C. J.:J. Phys. Chem. 81, 1331 (1977).
Lewis, J. W. and Sandorfy, C.:Can. J. Chem. 60, 1720 (1982).
Barbara, P. F., Rentzepis, P. M., and Brus, L. E.:J. Am. Chem. Soc. 102, 2786 (1980).
Ledbeter, J. W.:J. Phys. Chem. 86, 2449 (1982).
Lee, H. and Kitagawa, T.:Bull. Chem. Soc. Jpn. 59, 2897 (1986).
Grummt, U. W.:Journal of prakt. Chemie 327, 220 (1985).
Lambi, E., Gegiou, D., and Hadjoudis, E.:J. Photochem. Photobiol. A: Chem. 86, 241 (1995).
Khudyakov, I. V., Turro, N. J., and Yakushento, I. K.:J. Photochem. Photobiol. A: Chem. 63, 25 (1992).
Kawamura, S., Tsutsui, T., Saito, S., Murao, Y., and Khia, K.:J. Am. Chem. Soc. 110, 509 (1988).
Goodman, M. and Kossoy, A.:J. Am. Chem. Soc. 88, 5010 (1966); Goodman, M. and Falxa, M. L.:J. Am. Chem. Soc. 89, 3863 (1967).
Ueno, A., Anzai, J., Osa, T., and Kadoma, Y.:Bull. Chem. Soc. Jpn. 52, 549 (1979).
Pieroni, O., Houben, J. L., Fissi, A., Costantino, P., and Ciardelli, F.:J. Am. Chem. Soc. 102, 5913 (1980).
Holderbaum, M., Durr, H., and Hadjoudis, E.:J. Photochem. Photobiol. A: Chem. 58, 1 (1991).
Hauck, G. and Durr, H.:Angew. Chem. Int. Ed. Engl. 18, 945 (1979).
Hadjoudis, E., Kondilis, P., Mavridis, I., and Tsoucaris, G.: inAdvances in Inclusion Science, Huber, A. and Szejtli, J., Eds., Kluwer Academic Publishers, Dordrecht (1988), p. 119.
Pistolis, G., Gegiou, D., and Hadjoudis, E.:J. Photochem. Photobiol. A: Chem. in press (1995).
Durr, H.: inMolecules and Systems, Durr, H. and Bouas-Laurent, H., Eds., Elsevier, Amsterdam (1990), p. 1.
Andes, R. V. and Manikowski, D. M.:Appl. Opt. 7, 1179 (1968).
Kumar, G. S. and Neckers, D. C.:Chem. Rev. 89, 1915 (1989).
Ottorstedt, J-E. A.: cited in Pater, R.:J. Heterocyclic Chem. 7, 1113 (1970).
Gooden, E. W.:Nature 203, 515 (1964); Gooden, E. W.:Austr. J. Chem. 18, 637 (1965).
Cohen, M. D. and Hadjoudis, E.:Mol. Cryst. 2, 267 (1967).
Hadjoudis, E., Ward, T. A., and Milia, F.: inProceedings of the Second International Symposium on NQR Spectroscopy, Colligiani, A., Vallerini, A., Eds., Pisa (1975), p. 153.
Sharma, K. S., Bhushan, K., and Singh, G.P.:J. Photochem. Photobiol., A: Chem. 52, 473 (1990).
Cook, M. J. and Thomson, A. J.:Chem. Ber. 20, 914 (1984).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Hadjoudis, E. Photochromic and thermochromic anils. Mol Eng 5, 301–337 (1995). https://doi.org/10.1007/BF01004014
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01004014