4-(2,2′-Bipyridine-5-yl)benzaldehyde as a novel fluorescent reagent for Zn2+ with emission in the near-infrared region

Sensors and Actuators, B: Chemical

Volumn 135, Issue 2, 2009, Pages 512-515

  Lin, Weiying ^a   Feng, Jianbo ^a   Yuan, Lin ^a   Tan, Wen ^a  

^a HUNAN UNIVERSITY   (China)

Author keywords

Bipyridyl; Chemosensor; Fluorescent reagents; Near infrared; Zinc ions

Indexed keywords

ALDEHYDES; DRUG PRODUCTS; EMISSION SPECTROSCOPY; INFRARED DEVICES; INFRARED SPECTROSCOPY; IONS; METAL IONS; OPTICAL PROPERTIES; ZINC;

BIPYRIDYL; CHEMOSENSOR; FLUORESCENT REAGENTS; NEAR-INFRARED; ZINC IONS;

FLUORESCENCE;

EID: 57949093703     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2008.09.036     Document Type: Article

References (34)

1. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97 (1996) 1515-1566
2. Callan J.F., de Silva A.P., and Magri D.C. Luminescent sensors and switches in the early 21st century. Tetrahedron 61 (2005) 8551-8588
3. Kiyose K., Kojima H., and Nagano T. Functional near-infrared fluorescent probes. Chem. Asian J. 3 (2008) 506-515
4. Weissleder R., and Ntziachristos V. Shedding light onto live molecular targets. Nat. Med. 9 (2003) 123-128
5. Weissleder R. A clearer vision for in vivo imaging. Nat. Biotechnol. 19 (2001) 316-317
6. Frangioni J.V. In vivo near-infrared fluorescence imaging. Curr. Opin. Chem. Biol. 7 (2003) 626-634
7. Berg J.M., and Shi Y. The galvanization of biology: a growing appreciation for the roles of zinc. Science 271 (1996) 1081-1085
8. Vallee B.L., and Falchuk K.H. The biochemical basis of zinc physiology. Physiol. Rev. 72 (1993) 79-118
9. Choi D.W., and Koh J.Y. Zinc and brain injury. Annu. Rev. Neurosci. 21 (1998) 347-375
10. 2+: a novel ionic mediator of neural injury in brain disease. Trends Pharm. Sci. 21 (2000) 395-401
11. Canzoniero L.M.T., Turetsky D.M., and Choi D.W. Measurement of intracellular free zinc concentrations accompanying zinc-induced neuronal death. J. Neurosci. 19 (1999) RC31
12. Pérez-López M., de Mendoza M.H., Beceiro A.L., and Rodríguez F.S. Heavy metal (Cd, Pb, Zn) and metalloid (As) content in raptor species from Galicia (NW Spain). Ecotoxicol. Environ. Saf. 70 (2008) 154-162
13. Sanders M., Preez H.D., and Vuren J.V. Monitoring cadmium and zinc contamination in freshwater systems with the use of the freshwater river crab, Potamonautes warreni. Water SA 22 (1999) 91-98
14. 2+. J. Am. Chem. Soc. 127 (2005) 14962-14963
15. Wang B., and Wasielewski M.R. Design and synthesis of metal ion-recognition-induced conjugated polymers: an approach to metal ion sensory materials. J. Am. Chem. Soc. 119 (1997) 12-21
16. Kokil A., Yao P., and Weder C. Organometallic networks based on 2,2′-bipyridine-containing poly(p-phenylene ethynylene)s. Macromolecules 38 (2005) 3800-3807
17. Davies I.W., Marcoux J.-F., Wu J., Palucki M., Corley E.G., Robbins M.A., Tsou N., Ball R.G., Dormer P., Larsen R.D., and Reider P.J. An efficient preparation of vinamidinium hexafluorophosphate salts. J. Org. Chem. 65 (2000) 4571-4574
18. Kuwabara H., Umihara K., Furugori Y., and Itoh I. Efficient preparation of 2-pyridylpyridines using β-N,N-dialkylated aminoacroleins or their equivalent as vinadinium tetrafluoroborate. Chem. Lett. 34 (2005) 834-835
19. Marcoux J.-F., Marcotte F.-A., Wu J., Dormer P.G., Davies I.W., Hughes D., and Reider P.J. A general preparation of pyridines and pyridones via the annulation of ketones and esters. J. Org. Chem. 66 (2001) 4194-4199
20. Nijegorodov N.I., and Downey W.S. The influence of planarity and rigidity on the absorption and fluorescence parameters and intersystem crossing rate constant in aromatic molecules. J. Phys. Chem. 98 (1994) 5639-5643
21. McFarland S.A., and Finney N.S. Fluorescent chemosensors based on conformational restriction of a biaryl fluorophore. J. Am. Chem. Soc. 123 (2001) 1260-1261
22. McFarland S.A., and Finney N.S. Fluorescent signaling based on control of excited state dynamics. Biarylacetylene fluorescent chemosensors. J. Am. Chem. Soc. 124 (2002) 1178-1179
23. Choi K., and Hamilton A.D. A dual channel fluorescence chemosensor for anions involving intermolecular excited state proton transfer. Angew. Chem. Int. Ed. 40 (2001) 3912-3915
24. Vosburgh W.C., and Cooper G.R. Complex ions. I. The identification of complex ions in solution by spectrophotometric measurements. J. Am. Chem. Soc. 63 (1941) 437-442
25. 2+ in a micellar medium. Org. Lett. 9 (2007) 121-124
26. Benesi H.A., and Hildebrand J.H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71 (1949) 2703-2707
27. Coskun A., and Akkaya E.U. Ion sensing coupled to resonance energy transfer: a highly selective and sensitive ratiometric fluorescent chemosensor for Ag (I) by a modular approach. J. Am. Chem. Soc. 127 (2005) 10464-10465
28. Coskun A., and Akkaya E.U. Signal ratio amplification via modulation of resonance energy transfer: proof of principle in an emission ratiometric Hg (II) sensor. J. Am. Chem. Soc. 128 (2006) 14474-14475
29. Rurack K. Flipping the light switch 'ON' - the design of sensor molecules that show cation-induced fluorescence enhancement with heavy and transition metal ions. Spectrochim. Acta A 57 (2001) 2161-2195
30. Ma Y., Luo W., Quinn P.J., Liu Z., and Hider R.C. Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors. J. Med. Chem. 47 (2004) 6349-6362
31. 2+ metal ions. J. Org. Chem. 64 (1999) 7034-7039
32. 2+-responsive probe, operating above 500 nm. J. Am. Chem. Soc. 125 (2003) 3418-3419
33. Caruso J.A., Popov A.I., Chantooni Jr. M.K., Ringbom A., Csányi L.J., Rosenthal D., Högfeldt E., Steigman J., Kolthoff I.M., Wänninen E., Linck R.G., Zuman P., and Perrin D.D. In: Kolthoff I.M., and Elving P.J. (Eds). Treatise on Analytical Chemistry. Part I: Theory and Practice. 2nd ed. vol. 2 (1979), John Wiley & Sons, New York 609-611 (Chapter 21)
34. Guo L., Hong S., Lin X., Xie Z., and Chen G. An organically modified sol-gel membrane for detection of lead ion by using 2-hydroxy-1-naphthaldehydene-8-aminoquinoline as fluorescence probe. Sens. Actuators B 130 (2008) 789-794