Benzothiazolium styryl dyes containing a monoazacrown ether: Protonation and complexation with metal and ammonium cations in solution

(Note: The full text of this document is currently only available in the PDF Version )

Igor K. Lednev, Ronald E. Hester and John N. Moore


Abstract

Solutions of the trans-isomers of a model benzothiazolium styryl dye and two novel derivatives containing monoaza-15-crown-5 and -18-crown-6 ether rings have been studied using UV–VIS absorption spectroscopy. Protonation of these dyes causes the strongest colour changes, arising from hypsochromic shifts of ca. 140 nm in their absorption band maxima. The azacrown ether dyes have been found to complex alkali-metal (Li+, Na+, and K+), alkaline-earth-metal (Mg2+, Ca2+, and Ba2+), and ammonium (NH4+) cations, but not silver (Ag+), in acetonitrile solution, while of these cations only Ag+ forms a complex in aqueous solution. Spectra and stability constants are reported for all of these complexes and indicate that the dyes are effective chromoionophores. The stability of the metal cation complexes in acetonitrile solution has been found to depend on the presence of trace amounts of water; this effect has been quantified and is interpreted in terms of the competitive solvation of these cations by water. The stability constants, spectra, and hypsochromic shifts together indicate that small cations complex with the crown ether ring, but not with the azacrown nitrogen atom.


References

  1. R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 1995, 95, 2529 CrossRef CAS.
  2. Cation Binding by Macrocycles: Complexation of Cationic Species by Crown Ethers, ed. Y. Inoue and G. W. Gokel, Marcel Dekker, New York, 1990 Search PubMed.
  3. M. Mitewa and P. R. Bontchev, Coord. Chem. Rev., 1994, 135/136, 129 CrossRef.
  4. L. F. Lindoy, in ref. 2, p. 599.
  5. A. Mason, A. Sheridan, I. O. Sutherland and A. Vincent, J. Chem. Soc., Chem. Commun., 1994, 2627 RSC.
  6. M. Takagi, in ref. 2, p. 465.
  7. L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 1995, 197 RSC.
  8. P. D. Beer, in Advances in Inorganic Chemistry, ed. A. G. Sykes, Academic Press, San Diego, 1992, vol. 39, p. 79 Search PubMed.
  9. R. Dieing, V. Morisson, A. J. Moore, L. M. Goldenberg, M. R. Bryce, J.-M. Raoul, M. C. Petty, J. Garín, M. Savirón, I. K. Lednev, R. E. Hester and J. N. Moore, J. Chem. Soc., Perkin Trans. 2, 1996, 1587 RSC.
  10. A. E. Kaifer and L. Echegoyen, in ref. 2, p. 363.
  11. A. P. de Silva and C. P. McCoy, Chem. Ind. (London), 1994, 992 CAS.
  12. G. W. Gokel, Chem. Soc. Rev., 1992, 39 RSC.
  13. H. K. Frensdorff, J. Am. Chem. Soc., 1971, 93, 600 CrossRef CAS.
  14. D. A. Gustowski, V. J. Gatto, J. Mallen, L. Echegoyen and G. W. Gokel, J. Org. Chem., 1987, 52, 5172 CrossRef CAS.
  15. H. Zollinger, Color Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments, VCH, Weinheim, 1987 Search PubMed.
  16. J. D. Wright, Chem. Br., 1995, 374 Search PubMed.
  17. H. Mrozek, H. Nikol, A. Vogler and F. Vögtle, J. Photochem. Photobiol. A, 1994, 84, 227 CrossRef CAS.
  18. J. Bourson, J. Pouget and B. Valeur, J. Phys. Chem., 1993, 97, 4552 CrossRef CAS.
  19. J. F. Létard, R. Lapouyade and W. Rettig, Pure Appl. Chem., 1993, 65, 1705 CrossRef CAS.
  20. M. Inouye, M. Ueno, T. Kitao and K. Tsuchiya, J. Am. Chem. Soc., 1990, 112, 8977 CrossRef CAS.
  21. J. P. Dix and F. Vögtle, Chem. Ber., 1980, 113, 457 CrossRef CAS.
  22. B. Valeur and E. Bardez, Chem. Br., 1995, 31, 216 Search PubMed.
  23. J. F. Létard, R. Lapouyade and W. Rettig, Mol. Cryst. Liq. Cryst., 1993, 236, 41 Search PubMed.
  24. J. Bourson and B. Valeur, J. Phys. Chem., 1989, 93, 3871 CrossRef CAS.
  25. S. Fery-Forgues, M. T. Le Bris, J. P. Guette and B. Valeur, J. Phys. Chem., 1988, 92, 6233 CrossRef CAS.
  26. K. Kimura, Coord. Chem. Rev., 1996, 148, 41 CrossRef CAS.
  27. M. V. Alfimov, S. P. Gromov and I. K. Lednev, Chem. Phys. Lett., 1991, 185, 455 CrossRef CAS.
  28. I. K. Lednev, O. A. Fyedorova, S. P. Gromov, M. V. Alfimov, J. N. Moore and R. E. Hester, Spectrochim. Acta, Part A, 1993, 49, 1055 CrossRef.
  29. M. V. Alfimov, Y. V. Fedorov, O. A. Fedorova, S. P. Gromov, R. E. Hester, I. K. Lednev, J. N. Moore, V. P. Oleshko and A. I. Vedernikov, J. Chem. Soc., Perkin Trans. 2, 1996, 1441 RSC.
  30. I. K. Lednev and M. C. Petty, Adv. Mater., 1996, 8, 615 CrossRef.
  31. I. K. Lednev, R. E. Hester and J. N. Moore, J. Am. Chem. Soc., in press Search PubMed.
  32. S. P. Gromov, E. N. Ushakov, O. A. Fedorova, V. A. Soldatenkova and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., submitted Search PubMed.
  33. B. Brzezinski, G. Schroeder, A. Rabold and G. Zundel, J. Phys. Chem., 1995, 99, 8519 CrossRef CAS.
  34. J. F. Létard, S. Delmond, R. Lapouyade, D. Braun, W. Rettig and M. Kreissler, Recl. Trav. Chim. Pays-Bas, 1995, 114, 517 CAS.
  35. Y. Inoue, Y. Liu and T. Hakushi, in ref. 2, p. 1.
  36. E. N. Ushakov, O. B. Stanislavsky, S. P. Gromov, O. A. Fedorova and M. V. Alfimov, Dokl. Akad. Nauk SSSR, 1992, 323, 702 Search PubMed.
  37. A. F. Solotnov, V. P. Solovev, L. V. Govorkova, T. N. Kudrya, A. A. Chaikovskaya and O. A. Raevskii, Koord. Khim., 1989, 15, 319 Search PubMed.
  38. M. V. Alfimov, A. V. Churakov, Y. V. Fedorov, O. A. Fedorova, S. P. Gromov, R. E. Hester, J. A. K. Howard, L. G. Kuz'mina, I. K. Lednev and J. N. Moore, in preparation.
  39. K. Izutsu, T. Nomura, T. Nakamura, H. Kazama and S. Nakajima, Bull. Chem. Soc. Jpn., 1974, 47, 1657 CAS.
  40. M. K. Chantooni and I. M. Kolthoff, J. Am. Chem. Soc., 1967, 89, 1582 CrossRef CAS.
  41. D. A. Johnson, Some Thermodynamic Aspects of Inorganic Chemistry, Cambridge University Press, Cambridge, 1982 Search PubMed.
  42. W. E. Dasent, Inorganic Energetics, Cambridge University Press, Cambridge, 1982 Search PubMed.
  43. R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 1991, 91, 1721 CrossRef CAS.
  44. C. J. Pedersen, J. Am. Chem. Soc., 1970, 92, 386 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.