From p-dimethoxybenzene to crown-benzenophanes, 4: Cation-complexing properties of Bis(p-phenylene-34-crown-10) - A structural and spectrophotometric study

Liebigs Annales

Volumn , Issue 1, 1997, Pages 97-106

  Marquis, Damien ^a   Greiving, Helmut ^c   Desvergne, Jean Pierre ^a   Lahrahar, Nacer ^b   Marsau, Pierre ^b   Hopf, Henning ^c   Bouas Laurent, Henri ^a  

^a CNRS   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

^c TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Binding constants of metal cations; Crown ethers; Fluorescence

Indexed keywords

EID: 0011212063     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970115     Document Type: Article

References (73)

1. [1a] G. W. Gokel, Crown Ethers and Cryptands (Ed.: J. F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991.
2. [1b] F. Diederich, Cyclophanes (Ed.: J. F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991.
3. [1c] F. Vögtle, Supramolecular Chemistry, VCH, Weinheim, FRG, 1991.
4. [1d] C. D. Gutsche, Calixarenes (Ed.: J. F. Stoddart), The Royal Society of Chemistry, Cambridge, 1989.
5. [1e] P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 193-218.
6. [1f] D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godínez, T. Goodnow, A. E. Kaifer, S. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 1271-1293.
7. [1g] D. J. Cram, J. M. Cram, Container Molecules and their Guests (Ed.: J. F. Stoddart), The Royal Society of Chemistry, Cambridge, 1994.
8. [1h] H. J. Schneider, H. Dürr, Frontiers in Supramolecular Organic Chemistry and Photochemistry, VCH, Weinheim, 1991.
9. [1i] V. Balzani, L. De Cola, Supramolecular Chemistry, Kluwer Academic Publishers, The Netherlands, 1992.
10. [1j] L. F. Lindoy, The Chemistry of Macrocyclic Ligand Complexes, Cambridge University Press, Cambridge, 1989.
11. [1k] J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1994.
12. [1l] R. Utermöhlen, H. Hopf, P. G. Jones, P. Bubenitschek, J.-P. Desvergne, H. Bouas-Laurent, J. Chem. Res. (S), 1994, 260-261,
13. R. Utermöhlen, H. Hopf, P. G. Jones, P. Bubenitschek, J.-P. Desvergne, H. Bouas-Laurent, J. Chem. Res. ((M), 1546-1566.
14. [2a] R. Y. Tsien, Annu. Rev. Neurosci. 1989, 12, 227.
15. [2b] R. Y. Tsien, Am. J. Physiol. 1992, C723, 263.
16. [1c] M. Y. Chae, A. W. Czarnik, J. Am. Chem. Soc. 1992, 114, 9704-9705.
17. [2d] E. U. Akkaya, M. E. Huston, A. W. Czarnik, J. Am. Chem. Soc. 1990, 112, 3590-3593.
18. [3a] L. R. Sousa, J. M. Larson, J. Am. Chem. Soc. 1977, 99, 307-310.
19. [3b] R. A. Bissel, A. P. De Silva, H. Q. N. Gunaratne, P. L. Lynch, G. E. M. Maeuire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187-195.
20. [3c] Fluorescent Chemosensors for Ion and Molecule Recognition (Ed.: A. W. Czarnik), ACS Symposium Series No. 538, American Chemical Society, Washington DC, 1993.
21. [3d] F. Vögtle, P. Knops, Angew. Chem. Int. Ed. Engl. 1991, 30, 958-960.
22. [3e] A. F. Scholl, I. O. Sutherland, J. Chem. Soc., Chem. Commun. 1992, 1716-1718.
23. [1f] R. Baldes, H. J. Schneider, Angew. Chem. Int. Ed. Engl. 1995, 34, 321-323;
24. Angew. Chem. 1995, 107, 380-383.
25. [3g] I. Aoki, T. Sakaki, S. Shinkai, J. Chem. Soc., Chem. Commun. 1992, 730-732.
26. [3h] A. W. Czarnik, Acc. Chem. Res. 1994, 27, 302-308.
27. [3i] H. Bouas-Laurent, A. Castellan, M. Daney, J.-P. Desvergne, G. Guinand, P. Marsau, M.-H. Riffaud, J. Am. Chem. Soc. 1986, 108, 315-317.
28. [3j] D. Marquis, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1995, 60, 7984-7996.
29. [3k] J. Bourson, J. Pouget, B. Valeur, J. Phys. Chem. 1993, 97, 17, 4552-4557.
30. [3l] V. Balzani, J.-M. Lehn, J. Van de Loosdrecht, A. Mecati, N. Sabbatini, R. Ziessel, Angew. Chem. Int. Ed. Engl. 1991, 50, 190-191;
31. Angew. Chem. 1991, 103, 186-187.
32. [4a] A. Lüttringhaus, Annalen der Chemie 1937, 528, 181-227.
33. [4b] R. M. Izatt, J. J. Christensen, Synthetic Multidentate Macrocyclic Compounds, Academic Press Inc. 1978.
34. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036.
35. N. S. Poonia, A. V. Bajaj, Chem. Rev. 1979, 79, 389-445.
36. [7a] A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc., Chem. Commun. 1987, 1061-1064 and 1066-1070.
37. [7b] J. F. Stoddart, Pure Appl Chem. 1988, 60, 467-472.
38. [7c] R. C. Helgeson, T. L. Tarnovski, J. M. Timko, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 6411-6418.
39. [7d] D. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828.
40. [8a] H. Hopf, R. Utermöhlen, P. G. Jones, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1992, 57, 5509-5517.
41. [8b] P. Marsau, H. Adrianatoandro, T. Willms, J.-P. Desvergne, H. Bouas-Laurent, H. Hopf, P. G. Jones, R. Utermohlen, Chem. Ber. 1993, 126, 1441-1446.
42. B. L. Allwood, N. Spencer, H. Shahriari-Zavareh, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1987, 1061-1064.
43. J. D. Owen, J. Chem. Soc., Dalton Trans. 1978, 1418-1423.
44. M. A. Neuman, E. C. Steiner, F. P. Van Remoortere, F. P. Boer, Inorg. Chem. 1975, 14, 734-740.
45. G. Guinand, P. Marsau, H. Bouas-Laurent, A. Castellan, J.-P. Desvergne, M. Lamotte, Acta Crystallogr. 1987, C43, 857-860.
46. A. M. Manotti-Lanfredi, M. A. Pellinghelli, A. Tiripicchio, M. Tiripicchio Camellini, Acta Crystallogr. 1972, B28, 679-682.
47. M. M. Borel, M. Ledesert, Acta Crystallogr. 1975, B31, 725-728.
48. R. A. Wood, V. J. James, S. J. Angyal, Acta Crystallogr. 1972, B33, 2248-2241.
49. D. E. Fenton, D. H. Cook, I. W. Nowell, P. E. Walker, J. Chem. Soc., Chem. Commun. 1977, 623-624.
50. H.-G. Löhr, F. Vögtle, Acc. Chem. Res. 1985, 18, 65-72.
51. [8a] J. B. Birks, Photophysics of Aromatic Molecules, Wiley Interscience, New York, 1970, pp. 208-211.
52. [18b] M. Kasha, J. Chem. Phys. 1952, 20, 71.
53. [9a] M. M. Martín, P. Plaza, N. D. Hung, Y. H. Meyer, J. Bourson, B. Valeur, Chem. Phys. Lett. 1993, 202, 425.
54. [19b] J.-F. Létard, S. Delmond, R. Lapouyade, D. Braun, W. Rettig, M. Kreisler, Recl. Trav. Chim. Pays-Bas 1995, 114, 517-527.
55. [19c] K. Kimura, M. Kaneshice, M. Yokoyama, Chem. Mater. 1995, 7, 945-950.
56. J.-P. Desvergne, J. Lauret, H. Bouas-Laurent, P. Marsau, N. Lahrahar, H. Adrianatoandro, M. Cotrait, Recl. Trav. Chim. Pays-Bas 1995, 114, 504-513.
57. L. G. Sillen, B. Warnquist, Ark. Kemi. 1968, 31, 315-339 and 377-390.
58. R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen, D. Sen, Chem. Rev. 1985, 85, 271-339.
59. N. S. Poonia, J. Am. Chem. Soc. 1974, 96, 1012-1018.
60. J. D. Owen, Acta Cryst. 1984, C40, 951.
61. H. Bauer, J. Briaire, H. A. Staab, Tetrahedron Lett. 1985, 26, 50, 6175-6178.
62. [26a] T. G. Traylor, M. J. Mitchell, J. P. Ciccone, S. Nelson, J. Am. Chem. Soc. 1982, 104, 4986-4989.
63. [26b] I. Tabushi, S.-I. Kugimiya, M. G. Kinnaird, T. Sasaki, J. Am. Chem. Soc. 1985, 107, 4192-4199.
64. [26c] J. Rebek Jr., T. Costello, L. Marshall, R. Wattley, R. C. Gadwood, K. Onan, J. Am. Chem. Soc. 1985, 107, 7481-7487.
65. [26d] M. Gubelmann, A. Harriman, J.-M. Lehn, J. Sessler, J. Chem. Soc., Chem. Commun. 1988, 77-79.
66. [26e] J. Rebek Jr., R. Wattley, T. Costello, R. C. Gadwood, L. Marshall, Angew. Chem. Int. Ed. Engl. 1981, 20, 605-606;
67. Angew. Chem. 1981, 93, 584-585.
68. [26f] Y. Kobuke, K. Kokubo, M. Munakata, J. Am. Chem. Soc. 1995, 117, 12751-12758.
69. T. de Roeck, N. Boens, J. Dockx, DECAN (1.0), Copyright 1991, Leuven, Belgium.
70. J. Dale, P. O. Kristiansen, Acta Chem. Scand. 1971, 26, 1471-1478.
71. [1f].
72. L. Pauling, The Nature of the Chemical Bond 1945, 2nd ed., Ithaca, Cornell Univ. Press, pp. 350.
73. C. J. Gilmore, MITHRIL, Computer Program for the Automatic Solution of Crystal Structures from X-ray Data, Department of Chemistry, University of Glaseow, Scotland, 1983.