Novel preorganized hemispherands to encapsulate rare earth ions: Shielding and ligand deuteration for prolonged lifetimes of excited Eu3+ ions

Journal of the American Chemical Society

Volumn 119, Issue 1, 1997, Pages 138-144

  Oude Wolbers, Manon P ^a   Van Veggel, Frank C J M ^a   Snellink Ruël, Bianca H M ^a   Hofstraat, Johannes W ^a,b   Geurts, Frank A J ^a,b   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

LANTHANIDE; MACROCYCLIC COMPOUND; METAL ION;

ARTICLE; COMPLEX FORMATION; ENCAPSULATION; LUMINESCENCE; MASS SPECTROMETRY; MOLECULAR DYNAMICS; PHYSICS; THEORY;

EID: 0031049708     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9609314     Document Type: Article

References (52)

1. (a) Horrocks, W. DeW., Jr.; Albin, M. Proc. Inorg. Chem. 1984, 31, 1-104.
2. (b) Sabbatini, N.; Guardigli, M.; Lehn, J.-M. Coord. Chem. Rev. 1993, 123, 210-228.
3. Ermolaev, V. L.; Sveshnikova, E. B. Russ. Chem. Rev. 1994, 63, 905-922 and references cited therein.
4. (a) Horrocks, W. DeW., Jr.; Sudnick, D. R. Acc. Chem. Res. 1981, 14, 384-392.
5. (b) Holz, R. C.; Chang, C. A.; Horrocks, W. DeW., Jr. Inorg. Chem. 1991, 30, 3270-3275.
6. (a) Alpha, B.; Lehn, J.-M.; Mathis, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 259-261.
7. (b) Alpha, B.; Balzani, V.; Lehn, J.-M.; Perathoner, S.; Sabbatini, N. Angew. Chem., Int. Ed. Engl. 1987, 26, 1266-1267.
8. (c) Alpha, B.; Ballardini, R.; Balzani, V.; Lehn, J.-M.; Perathoner, S.; Sabbatini, N. Photochem. Photobiol. 1990, 52, 299-306.
9. (a) Aime, S.; Batsanov, A. S.; Botta, M.; Howard, J. A. K.; Parker, D.; Senanayake, K.; Williams, G. Inorg. Chem. 1994, 33, 4696-4706.
10. (b) Balzani, V.; Lehn, J.-M.; Loosdrecht, J. v. d.; Mecati, A.; Sabbatini, N.; Ziessel, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 190-191.
11. (c) Prodi, L.; Maestri, M.; Ziessel, R.; Balzani, V. Inorg. Chem. 1991, 30, 3798-3802.
12. (d) Sabbatini, N.; Guardigli, M.; Bolletta, F.; Manet, I.; Ziessel, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1501-1503.
13. (e) Sabbatini, N.; Guardigli, M.; Manet, I.; Bolletta, F.; Ziessel, R. Inorg. Chem. 1994, 33, 955-959.
14. (a) Balzani, V.; Berghmans, E.; Lehn, J.-M.; Sabbatini, N.; Terörde, R.; Ziessel, R. Helv. Chim. Acta 1990, 73, 2083-2089.
15. (b) Mukkala, V.-M.; Helenius, M.; Hemmilä, I.; Kankare, J.; Takalo, H. Helv. Chim. Acta 1993, 76, 1361-1378.
16. (c) Li, M.; Selvin, P. R. J. Am. Chem. Soc. 1995, 117, 8132-8138.
17. (d) Selvin, P. R.; Jancarik, J.; Li, M.; Hung, L.-W. Inorg. Chem. 1996, 35, 700-705.
18. (a) Sabbatini, N.; Guardigli, M.; Mecati, A.; Balzani, V.; Ungaro, R.; Ghidini, E.; Casnati, A.; Pochini, A. J. Chem. Soc., Chem. Commun. 1990, 878-879.
19. (b) Sato, N.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1993, 621-624.
20. (c) Ulrich, G.; Ziessel, R. Tetrahedron Lett. 1994, 35, 6299-6302.
21. (d) Rudkevich, D. M.; Verboom, W.; Tol, E. v. d.; Staveren, C. J. v.; Kaspersen, F. M.; Verhoeven, J. W.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1995, 131-134.
22. (e) Steemers, F. J.; Verboom, W.; Reinhoudt, D. N.; Tol, E. v.d.; Verhoeven, J. W. J. Am. Chem. Soc. 1995, 117, 9408-9414.
23. (a) Kropp, J. L.; Windsor, M. W. J. Chem. Phys. 1965, 42, 1599-1608.
24. (b) Haas, Y.; Stein, G. J. Phys. Chem. 1971, 75, 3668-3677.
25. (a) Hemmilä, I.; Mukkala, V.-M.; Takalo, H. J. Fluoresc. 1995, 5, 159-163.
26. 3+ based on 1,4,7,10-tetraazacyclododecane, appeared: Dickins, R. S.; Parker, D.; de Sousa, A. S.; Williams, J. A. G. J. Chem. Soc., Chem. Commun. 1996, 697-698.
27. (a) Jungbluth, E. D. Laser Focus World 1991, 141.
28. (b) Desurvive, E. Sci. Am. 1992, 96-103.
29. (c) Dakss, M. L.; Miniscalco, W. J. SPIE Fiber Laser Sources Amplifiers II 1990, 1373, 111-124.
30. (d) Tropper, A.; Smart, R.; Perry, I.; Hanna, D.; Lincoln, J.; Brocklesby, B. SPIE Fiber Laser Sources Amplifiers II 1990, 1373, 152-157.
31. (e) Runge, P. K. AT&T Tech. J. 1992, 5-13.
32. Koenig, K. E.; Lein, G. M.; Stuckler, P.; Kaneda, T.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3553-3566.
33. Hey, H.; Arpe, H.-J. Angew. Chem., Int. Ed. Engl 1973, 12, 928-929.
34. The calculations were carried out following the protocol described in van Veggel, F. C. J. M.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1995, 114, 387-394.
35. 2O to prevent the exchange of deuterium atoms by hydrogens.
36. Rosenwald, R. H. J. Am. Chem. Soc. 1952, 74, 4602-4605.
37. Helgeson, R. C.; Czech, B. P.; Chapoteau, E.; Gebauer, C. R.; Kumar, A.; Cram, D. J. J. Am. Chem. Soc. 1989, 111, 6339-6350. The procedure was sligthly modified.
38. Olson, W. T.; Hipsher, H. F.; Buess, C. M.; Goodman, I. A.; Hart, I.; Lamneck, J. H., Jr; Gibbons, L. C. J. Am. Chem. Soc. 1947, 69, 2451-2454.
39. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483 and references cited therein.
40. 1H NMR spectroscopy and the solid state structure (Veggel, F. C. J. M. van; Duynhoven, J. P. M. v.; Harkema, S.; Oude Wolbers, M. P.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1996, 449-454).
41. Details of the simulations will be published elsewhere.
42. The excitation spectrum shows that excitation at 393 nm also gives partly sensitized emission.
43. 1.
44. 3+ is assumed to be constant.
45. -4 M can be excluded.
46. 3+ ion, leading to more allowed transitions.
47. 1 the lifetimes are still increased by a factor of about 1.3.
48. Förster, Th. Discuss. Faraday Soc. 1959, 27, 7-17.
49. 3 group of the coordinating methanol can have a decreasing effect on the lifetime.
50. Lakowicz, J. R. Principle of Fluorescence Spectroscopy, 2nd ed.; Plenum: New York, 1989; pp 52-57.
51. dec > 1800 °C).
52. 3+ no satisfactory elemental analysis could be obtained.