Anthryl-substituted heterocycles as acid-sensitive fluorescence probes

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 3929-3938

  Ihmels, Heiko ^a   Meiswinkel, Andreas ^b   Mohrschladt, Christian J ^b   Otto, Daniela ^a   Waidelich, Michael ^a   Towler, Michael ^c   White, Rick ^c   Albrecht, Martin ^a   Schnurpfeil, Alexander ^a,d  

^a UNIVERSITY OF SIEGEN   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c SAM HOUSTON STATE UNIVERSITY   (United States)

^d UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; ALCOHOLS; FLUORESCENCE; LIGHT ABSORPTION; PH EFFECTS; PROBES; SUBSTITUTION REACTIONS;

ACID-SENSITIVE FLUORESCENCE PROBES; ANTHRYL-SUBSTITUTED HETEROCYCLES; FLUOROPHORES; PROTONATION;

AROMATIC COMPOUNDS;

ACID; ANTHRACENE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CHLOROFORM; HETEROCYCLIC COMPOUND; OXAZOLINE DERIVATIVE; PYRIDINE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ACIDITY; ARTICLE; COMPARATIVE STUDY; CONCENTRATION (PARAMETERS); FLUORESCENCE; PH; PROTON TRANSPORT; SUBSTITUTION REACTION;

EID: 18744402495     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047841z     Document Type: Article

References (48)

1. (a) Optical Sensors; Wolfbeis, O. S., Ed.; Springer-Verlag: Heidelberg, 2004.
2. (b) Mohr, G. J. Chem. Eur. J. 2004, 10, 1082-1090.
3. (c) Pu, L. Chem. Rev. 2004, 104, 1687.
4. (d) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.
5. (e) Wiskur, S. L.; Ait-Haddou, H.; Anslyn, E. V.; Lavigne, J. J. Acc. Chem. Res. 2001, 34, 963.
6. (f) Chemosensors of Ion and Molecular Recognition; Desvergne, J.-P., Czarnik, A. W., Eds.; Kluwer Academic Press: Dordrecht, The Netherlands, 1997.
7. (g) de Silva, A. P. H.; Gunaratne, Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
8. (h) Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; ACS Symposium Series No. 538; American Chemical Society: Washington DC, 1993.
9. (i) Valeur, B. In Topics in Fluorescence Spectroscopy, Vol. 4: Probe Design and Chemical Sensing; Lakowicz, J. R., Ed.; Plenum Press: New York, 1994; Chapter 2.
10. (a) Sauer, M. Angew. Chem. 2003, 115, 1834;
11. Angew. Chem., Int. Ed. Engl. 2003, 42, 1790.
12. (b) Ambrose, W. P.; Goodwin, P. M.; Jett, J. H.; van Orden, A.; Werner, J. H.; Keller, R. A. Chem. Rev. 1999, 99, 2929.
13. (c) Ha, T.; Chemla, D. S.; Enderle, T.; Weiss, S. Bioimaging 1997, 55, 99.
14. (a) Bourson, J.; Pouget, J.; Valeur, B. J. Phys. Chem. 1993, 97, 4552.
15. (b) Dix, J. P.; Vögtle, F. Chem. Ber. 1981, 14, 638.
16. (c) Jones, G., II; Jiminez, J. A. C. J. Photochem. Photobiol. B: Biology 2001, 65, 5.
17. (d) Fayed, T. A. J. Photochem. Photobiol. A: Chemistry 1999, 121, 17.
18. (e) Corrent, S.; Hahn, P.; Pohlers, G.; Connolly, T. J.; Scaiano, J. C.; Fornes, V.; Garcia, H. J. Phys. Chem. B 1998, 102, 5852.
19. (f) Wolfbeis, O. S.; Marhold, H. Chem. Ber. 1985, 118, 3664.
20. For recent examples see: (a) Charier, S.; Ruel, O.; Baudin, J.-B.; Alcor, D.; Allemand, J.-F.; Meglio, A.; Jullien, L. Angew. Chem. 2004, 43, 4785;
21. Angew. Chem., Int. Ed. Engl. 2004, 116, 4889.
22. (b) Cui, D.; Quian, X.; Liu, F.; Zhang, R. Org. Lett. 2004, 6, 2757.
23. (c) Diwu, Z.; Chen, C.-S.; Zhang, C.; Klaubert, D. H.; Haugland, R. P. Chem. Biol. 1999, 6, 411.
24. (d) Kermis, H. R.; Kostov, Y.; Harms, P.; Rao, G. Biotech. Prog. 2002, 18, 1047.
25. (e) Garreis, T.; Huber, C.; Wolfbeis, O. S.; Daub, J. J. Chem. Soc., Chem. Commun. 1997, 1717.
26. Ihmels, H.; Meiswinkel, A.; Mohrschladt, C. J. Org. Lett. 2000, 2, 2865.
27. Ihmels, H. Eur. J. Org. Chem. 1999, 1595.
28. Mohan, R.; Katzenellenbogen, J. A. J. Org. Chem. 1984, 49, 1238.
29. Dick, B.; Hohlneicher, G. Chem. Phys. Lett. 1981, 83, 615.
30. Reichardt, C. Chem. Rev. 1994, 94, 2319.
31. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Society of Chemistry: London, 1997.
32. Albert, A. Heterocyclic Chemistry, 2nd ed.; Athlone Press: London, 1968; Chapter 13.
33. Reichardt, C. Solvents and Solvent Effects on Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003; Chapter 4.2.
34. Ireland, J. F.; Wyatt, P. A. H. Adv. Phys. Org. Chem. 1976, 12, 131.
35. See, e.g.: Hirsch, T.; Port, H.; Wolf, H. C.; Miehlich, B.; Effenberger, F. J. Phys. Chem. B 1997, 101, 4525.
36. TURBOMOLE Version 5, Ahlrichs, R.; M. Bär, M.; Baron, H.-P.; Bauernschmitt, R.; Böcker, S.; Furche, F.; Haase, F.; Häser, M.; Horn, H.; Hättig, C.; Huber, C.; Huniar, U.; Kattanek, M.; Köhn, A.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A.; Schneider, U.; Sierka, M.; Treutler, O.; Unterreiner, B.; Arnim, M. V.; Weigend, F.; Weiss, P.; Weiss, H. Institut f. Physikalische Chemie, Universität Karlsruhe, Kaiserstr. 12, D-76128 Karlruhe, 1998.
37. Gaussian 03, Revision B.04: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T. Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 2003.
38. Scheiner, S.; Kar, T. J. Phys. Chem. B 2002, 106, 534.
39. Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
40. (a) Wang, S.-L.; Ho, T.-I. J. Photochem. Photobiol. A: Chem. 2000, 135, 119.
41. (b) Haroutounian, S. A.; Katzenellenbogen, J. A. Photochem. Photobiol. 1988, 47, 503.
42. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899.
43. (a) Stubbs, M.; McSheehy, P. M.; Griffiths, J. R.; Bashford, C. L. Mol. Med. Today 2000, 6, 15.
44. (b) Smith, C. A,; Sutherland-Smith, A. J.; Keppler, B. K.; Kratz, F.; Baker, E. N. J. Biol. Inorg. Chem. 1996, 1, 424.
45. Demas, J. N.; Crosby, G. A. Crosby, J. Phys. Chem. 1971, 75, 991.
46. Eaton, D. F. Pure Appl. Chem. 1988, 60, 1108.
47. Britton, H. T. S.; Robinson, R. A. J. Chem. Soc. 1931, 458.
48. Polster, J.; Lachmann H. Spectrometric Titrations - Analysis of Chemical Equilibria; VCH: Weinheim, 1989.