Tautomeric switching and metal-cation sensing of ligand-equipped 4-hydroxy-/4-oxo-1,4-dihydroquinolines

Chemistry - A European Journal

Volumn 18, Issue 23, 2012, Pages 7269-7277

  Todorov, Aleksandar R ^a   Nieger, Martin ^a   Helaja, Juho ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

molecular devices; quinolines; sensors; tautomerism; zinc

Indexed keywords

APROTIC MEDIA; DFT CALCULATION; FLUORESCENCE MEASUREMENTS; HIGHLY SENSITIVE; MOLECULAR DEVICE; MONODENTATES; NMR STUDIES; NON-POLAR; QUINOLINES; SOLUTION STUDY; STRUCTURAL CHANGE; TAUTOMERISM; X-RAY STRUCTURE;

CHELATION; DENSITY FUNCTIONAL THEORY; METAL IONS; METALS; METHANOL; PHENOLS; SENSORS; SWITCHING; TOLUENE; ZINC;

CADMIUM COMPOUNDS;

EID: 84861612102     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103868     Document Type: Article

References (35)

1. M. B. Smith, J. March, Advanced Organic Chemistry, 6 th ed., John Wiley & Sons, New York, 2007, pp. 98-105.
2. J. A. Joule, K. Mills, Heterocyclic chemistry, 5 th ed, Wiley-Blackwell Publishing, Chichester, 2010
3. C. P. Whitman, Keto-enol Tautomerism in: Enzymatic Reactions in Comprehensive Natural Product Chemistry, Vol.5 (Ed.:, C.D. Poulter.,), Elsevier Science, Oxford, 1999, pp. 31-50.
4. V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines, 2 nd ed., Wiley-VCH, Weinheim, 2008.
5. C. Reichardt, Solvent effects on the Position of Homogenous Chemical Equilibria in Solvents and Solvent Effects in Organic Chemistry, 3 rd ed., Wiley-VCH, Weinheim, 2003, pp. 93-145.
6. J.-A. Farrera, I. Canal, P. Hidalgo-Fernández, M. L. Pérez-García, O. Huertas, F. J. Luque, Chem. Eur. J. 2008, 14, 2277-2285.
7. L. Antonov, V. Deneva, S. Simeonov, V. Kurteva, D. Nedeltcheva, J. Wirz, Angew. Chem. 2009, 121, 8015-8018; Angew. Chem. Int. Ed. 2009, 48, 7875- 7878
8. Angew. Chem. Int. Ed. 2009, 48, 7875-7878
9. L. M. Antonov, V. B. Kurteva, S. P. Simeonov, V. V. Deneva, A. Crochet, K. M. Fromm, Tetrahedron 2010, 66, 4292-4297.
10. A. Gordon, A. R. Katritzky, Tetrahedron Lett. 1968, 9, 2767-2770
11. J. Frank, A. R. Katrintzky, J. Chem. Soc. Perkin Trans. 2 1976, 1428-1431
12. M. J. Cook, S. El-Abbady, A. R. Katriztky, C. Guimon, G. Pfister-Guillouzo, J. Chem. Soc. Perkin Trans. 2 1976, 1652-1656
13. P. Beak, J. B. Covington, J. M. Zeigler, J. Am. Chem. Soc. 1978, 100, 177-178
14. E. Murguly, T. B. Norsten, N. Branda, J. Chem. Soc., Perkin Trans. 2 1999, 2789-2794
15. B. Stanovnik, M. Tisler, A. Katritzky, O. V. Denisko, Advances in Heterocyclic Chemistry, Vol.91, 2006, pp. 1-134.
16. A. deLaCruz, J. Elguero, P. Goya, A. Martinez, W. Pfleidener, Tetrahedron 1992, 48, 6135-6150.
17. N. Okabe, J. Miura. A. Shimosak, Acta Crystallogr. 1996, C52, 1827-1829.
18. G. Beretta, G. Vistoli, E. Caneva, C. Anselmi, R. M. Facino, Magn. Reson. Chem. 2009, 47, 456-459.
19. J.-J. Chen, L. W. Deady, M. F. Mackay, Tetrahedron 1997, 53, 12717-12728
20. A. Stankiewicz-Drogon, B. Dörner, T. Erker, A. M. Boguszewska-Chachulska, J. Med. Chem. 2010, 53, 3117-3126.
21. J. P. Michael, Nat. Prod. Rep. 2008, 25, 166-187.
22. S. Heeb, M. P. Fletcher, S. R. Chhabra, S. P. Diggle, P. Williams, M. Cámara, FEMS Microbiol. Rev. 2011, 35, 247-274.
23. E. D. Clercq, Nat. Rev. Microbiol. 2004, 2, 704-720
24. N. L. Oien, R. J. Brideau, T. A. Hopkins, J. L. Wieber, M. L. Knechtel, J. A. Shelly, R. A. Anstadt, P. A. Wells, R. A. Poorman, A. Huang, V. A. Vaillancourt, T. L. Clayton, J. A. Tucker, M. W. Wathen, Antimicrob. Agents Chemother. 2002, 46, 724-730.
25. P. S. Sherin, N. P. Gritsan, Y. P. Tsentalovich, Photochem. Photobiol. Sci. 2009, 8, 1550-1557.
26. L. Xue, C. Liu, H. Jiang, Org. Lett. 2009, 11, 1655-1658
27. H. Ito, M. Matsuoka, Y. Ueda, M. Takuma, Y. Kudo, K. Iguchi, Tetrahedron 2009, 65, 4235-4238.
28. B. Valeur, I. Leray, Coord. Chem. Rev. 2000, 205, 3-40.
29. M. J. Mphahlele, M. A. Fernandes, A. M. El-Nahas, H. Ottosson, S. M. Ndlovu, H. M. Sithole, B. S. Dladla, Danita DeWaal, J. Chem. Soc. Perkin Trans. 2 2002, 2159-2164.
30. G. Tucker, Jr., J. L. Irvin, J. Am. Chem. Soc. 1951, 73, 1923-1929.
31. The exceptional phase-dependent fluorescence behaviour presumably originates from rotational factors which may quench the fluorescence, that is,a benzyl group in themolecule:, A. Dreuw, J. Pötner, L. Lorenz, J. Wachtveitl, J. E. Djanhan, J. Brüning, T. Metz, M. Bolte, M. U. Schmidt, Angew. Chem. 2005, 117, 7961-7964
32. Angew. Chem. Int. Ed. 2005, 44, 7783-7786.
33. A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. Watson, R. Taylor, in Structure Correlation Vol.2 (Eds.:, H.-B. Bürgi, J.D. Dunitz,), VCH, Weinheim, 1994.
34. S. Rotzoll, H. Reinke, C. Fischer, P. Langer, Synthesis 2009, 1, 69-78.
35. Gaussian 09, Revision A.01; M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery,Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.