Novel fluorescence probes based on 2,6-donor-acceptor-substituted anthracene derivatives

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2865-2867

  Ihmels, Heiko ^a   Meiswinkel, Andreas ^a   Mohrschladt, Christian J ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; FLUORESCENT DYE;

ARTICLE; CHEMISTRY; SPECTROFLUOROMETRY; SYNTHESIS;

ANTHRACENES; FLUORESCENT DYES; SPECTROMETRY, FLUORESCENCE;

EID: 0034618308     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006291y     Document Type: Article

References (19)

1. (a) Chemosensors of Ion and Molecular Recognition; Desvergne J.-P., Czarnik, A. W., Eds.; Kluwer Academic Press: Dordrecht, The Netherlands, 1997; Vol. 492.
2. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
3. (c) Fluorescent Chemosensors for Ion and Molecule Recognition; ACS Symp. Ser. 538; Czarnik, A. W., Ed; American Chemical Society: Washington D. C., 1993.
4. (d) Valeur, B. In Topics in Fluorescence Spectroscopy; Lakowics, J. R., Ed.; Plenum Press: New York, 1994. Vol. 4; Chapter 2.
5. For recent examples, see (a) Ishikawa, J.; Sakamoto, H.; Nakao, S.; Wada, H. J. Org. Chem. 1999, 64, 1913.
6. (b) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209.
7. (c) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Marquis, D.; Pérez-García, L.; Stoddart, J. F. Eur. J. Org. Chem. 1998, 81.
8. (d) Hashimoto, K.; Kawaguchi, H.; Okuno, T.; Shirahama, H. Synlett 1997, 1202.
9. (e) Daub, J.; Beck, M.; Knorr, A.; Spreitzer, H. Pure Appl. Chem. 1996, 68, 1399.
10. (f) Vollmer, M. S.; Würthner, F.; Effenberger, F.; Emele, P.; Meyer, D. U.; Stümpfig, T.; Port, H.; Wolf, H. C. Chem. Eur. J. 1998, 4, 260.
11. Ihmels, H. Eur. J. Org. Chem. 1999, 1595.
12. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Society of Chemistry: London, 1997; Chapter 4.
13. PM3 calculations on the parent anthracene 1a reveal that the excited state (4.4 D) has a higher dipole moment than the ground state (3.0 D).
14. Reichardt, C. Chern. Rev. 1994, 94, 2319.
15. Koziar, J. C.; Cowan, D. O. Acc. Chem. Res. 1978, 11, 334.
16. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; McCoy, C. P.; Maxwell, P. R. S.; Rademacher, J. T.; Rice, T. E. Pure Appl. Chem. 1996, 68, 1443.
17. However, a major drawback of the system is the instability of the protonated oxazoline 1f-H, which decomposes slowly as was followed by the appearance of a new weak emission band after 24 h at room temperature. Experiments to design more stable protonated oxazolines are currently performed.
18. (a) Bourson, J., Pouget, J.; Valeur, B. J. Phys. Chem. 1993, 97, 4552.
19. b) Dix, J. P.; Vögtle, F. Chem. Ber. 1981, 14, 638.