A novel crown ether–cryptand photoswitch

Abstract

A new photoactive bis-anthracenyl crown undergoes a reversible photocyclisation to form a cryptand, with the efficiency of the forward reaction and the rate of the thermal reverse reaction strongly affected by the presence of cation substrates.

References

1. (a) J. M. Lehn, Supramolecular Chemistry—Concepts and Perspectives, VCH, Weinheim, 1995; (b) B. L. Feringa, W. F. Jager and B. de Lange, Tetrahedron, 1993, 49, 8267; (c) Chemosensors of Ion and Molecule Recognition, ed. J.-P. Desvergne and A. W. Czarnik, NATOASI Series C, vol. 492, Kluwer Academic Publishers, Dordrecht, 1997; (d) P. Tundo and J. H. Fendler, J. Am. Chem. Soc., 1980, 102, 4553; (e) A. Beeby, D. Parker and J. A. G. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 1565; (f) L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 1995, 24, 197.
2. H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau and M.-H. Riffaud, J. Am. Chem. Soc., 1986, 108, 315; R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maquire and K. R. A. S. Sandanayake, Chem. Soc. Rev., 1992, 187.
3. (a) J.-P. Desvergne and H. Bouas-Laurent, J. Chem. Soc., Chem. Commun., 1978, 403; (b) D. Marquis, J.-P. Desvergne and H. Bouas-Laurent, J. Org. Chem., 1995, 60, 7984; (c) G. Deng, T. Sakaki, K. Nakashima and S. Shinkai, Chem. Lett., 1992, 1287.
4. W. H. Pirkle and J. M. Finn, J. Org. Chem., 1983, 48, 2779.
5. J.-P. Desvergne, J. Rau, O. Cherkaoui, R. Zniber, H. Bouas-Laurent, N. Lahrahar, U. Meyer and P. Marsau, New J. Chem., 1996, 20, 881.
6. P. Marsau and N. Lahrahar, unpublished work.
7. D. Wang, Y. Ge, H. Hu, K. Yu and Z. Zhou, J. Chem. Soc., Chem. Commun., 1991, 685.
8. C. A. Hunter, J. Chem. Soc., Chem. Commun., 1991, 749; M. Shionoya, T. Ikeda, E. Kimura and M. Shiro, J. Am. Chem. Soc., 1994, 116, 3848.
9. For an irreversible example, see R. Warmuth, E. Grell, J. M. Lehn, J. W. Bats and G. Quinkert, Helv. Chim. Acta, 1991, 74, 671.