Synthesis, photophysics and electrochemistry of copper(I) diimine complexes containing thia-, selena- and tellura-crowns. A spectrochemical and luminescence ion probe for soft metal ions

Abstract

A series of copper(I) diimine complexes containing benzo-10-thia-15-crown-5, benzo-10-selena-15-crown-5, benzo-10-tellura-15-crown-5 and benzo-7,10,13-trithia-15-crown-5 moieties have been synthesized and characterized and their photophysics and electrochemistry studied. The encapsulation of soft metal ions by the cavity of the complexes has been investigated by electronic absorption and emission spectroscopy. The crystal structures of [Cu(PPh₃)₂(dic-S)]BF₄ and [Cu(PPh₃)₂(dic-Se)]BF₄ have been determined.

References

1. (a) C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 7017; (b) C. J. Pedersen, Angew. Chem., Int. Ed. Engl., 1988, 27, 1021.
2. J. M. Lehn, Struct. Bonding (Berlin), 1973, 16, 1; J. M. Lehn, Angew. Chem., Int. Ed. Engl., 1988, 27, 59.
3. D. J. Cram, Angew. Chem., Int. Ed. Engl., 1988, 27, 1009.
4. H. K. Frensdorff, J. Am. Chem. Soc., 1971, 93, 600.
5. J. J. Christensen, D. J. Eatough and R. M. Izatt, Chem. Rev., 1974, 74, 351.
6. M. Oue, K. Akama, K. Kimura, M. Tanaka and T. Shono, J. Chem. Soc., Perkin Trans. 1, 1989, 1675.
7. R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen and D. Sen, Chem. Rev., 1985, 85, 271.
8. R. D. Hancock, Pure Appl. Chem., 1986, 58, 1445; K. R. Adam, C. W. G. Ansell, K. P. Dancey, L. A. Drummond, A. J. Leong, L. F. Lindoy and P. A. Tasker, J. Chem. Soc., Chem. Commun., 1986, 1011; L. F. Lindoy, Pure Appl. Chem., 1989, 61, 1575.
9. V. W. W. Yam, K. K. W. Lo and K. K. Cheung, Inorg. Chem., 1995, 34, 4013.
10. (a) G. J. Kubas, Inorg. Synth., 1979, 19, 90; (b) J. Diez, S. Falagan, P. Gamasa and J. Gimeno, Polyhedron, 1988, 7, 37.
11. (a) N. I. Abakumova, I. K. Kolenko and M. I. Kodess, J. Org. Chem. USSR (Engl. Transl.), 1982, 18, 1305; (b) D. Landini, F. Montanari and F. Rolla, Synthesis, 1978, 223.
12. J. Dale and P. O. Kristiansen, Acta. Chem. Scand., 1972, 26, 1471.
13. M. S. Ptasinska, P. Telleman, V. M. L. J. Aarts, P. D. J. Grootenhuis, J. V. Eerden, S. Harkema and D. N. Reinhoudt, Tetrahedron Lett., 1987, 28, 1937.
14. D. W. Johnson, H. K. Mayer, J. P. Minard, J. Banaticla and C. Miller, Inorg. Chim. Acta, 1988, 144, 167.
15. A. D. Gedeonov and L. A. Pelevin, Radiokhimiya, 1987, 29, 401.
16. (a) R. R. Gagne, C. A. Koval and G. C. Lisensky, Inorg. Chem., 1980, 19, 2854; (b) C. M. Che, K. Y. Wong and F. C. Anson, J. Electroanal. Chem. Interfacial Electrochem., 1987, 226, 221.
17. (a) PATTY, P. T. Beurskens, G. Admiral, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits and C. Smykalla, the DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, 1992; (b) TeXsan, Crystal Structure Analysis Package, Molecular Structure Corporation, Houston, TX, 1985 and 1992.
18. L. M. Engelhardt, C. Pakawatchai, A. H. White and P. C. Healy, J. Chem. Soc., Dalton Trans., 1985, 125; J. R. Kirchhoff, D. R. McMillin, W. R. Robinson, D. R. Powell, A. T. McKenzie and S. Chen, Inorg. Chem., 1985, 24, 3928; C. Vogler, H. D. Hausen, W. Kaim, S. Kohlmann, H. E. A. Kramer and J. Rieker, Angew. Chem., Int. Ed. Engl., 1989, 28, 1659.
19. C. E. A. Palmer and D. R. McMillin, Inorg. Chem., 1987, 26, 3837; C. E. A. Palmer, D. R. McMillin, C. Kirmaier and D. Holten, Inorg. Chem., 1987, 26, 3167; D. R. McMillin, J. R. Kirchhoff and K. V. Goodwin, Coord. Chem. Rev., 1985, 64, 83; D. J. Casadonte and D. R. McMillin, J. Am. Chem. Soc., 1987, 109, 331; R. A. Rader, D. R. McMillin, M. T. Buckner, T. G. Matthews, R. K. Casadonte, S. B. Whittaker, L. M. Darmon and F. E. Lytle, J. Am. Chem. Soc., 1981, 103, 5906; A. A. Del Paggio and D. R. McMillin, Inorg. Chem., 1983, 22, 691; M. T. Buckner and D. R. McMillin, J. Chem. Soc., Chem. Commun., 1978, 759.
20. C. Kutal, Coord. Chem. Rev., 1990, 99, 213; R. F. Ziolo, S. Lipton and Z. Dori, Chem. Commun., 1970, 1124.
21. (a) J. Simon, M. K. Engel and C. Soulie, New J. Chem., 1992, 16, 287; (b) H. G. Hansma and D. E. Laney, Biophys. J., 1996, 70, 1933.
22. J. Bourson and B. Valeur, J. Phys. Chem., 1989, 93, 387; S. Frey-Forgues, M. T. Le Bris, J. P. Ginette and B. Valeur, J. Phys. Chem., 1988, 92, 6233.