Fluorescent and chromogenic probes bearing salicylaldehyde hydrazone functionality for cyanide detection in aqueous solution

Sensors and Actuators, B: Chemical

Volumn 143, Issue 1, 2009, Pages 171-176

  Sun, Yue ^a   Liu, Yunlong ^a   Guo, Wei ^a  

^a SHANXI UNIVERSITY   (China)

Author keywords

Chemosensor; Cyanide sensing; Fluorescence spectra; Salicylaldehyde hydrazone; UV vis spectra

Indexed keywords

CHEMOSENSOR; FLUORESCENCE SPECTRA; HYDRAZONES; SALICYLALDEHYDE; UV-VIS SPECTRA;

ALDEHYDES; BINDING ENERGY; BINDING SITES; FLUORESCENCE; FLUORINE CONTAINING POLYMERS; PROBES; STOICHIOMETRY;

CYANIDES;

EID: 71849103344     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2009.09.038     Document Type: Article

References (40)

1. Beer P.D., and Gale P.A. Anion recognition and sensing: the state of the art and future perspectives. Angew. Chem. Int. Ed. 40 (2001) 486
2. Amendola V., Esteban-Gómez D., Fabbrizzi L., and Licchelli M. What anions do to n-h-containing receptors. Acc. Chem. Res. 39 (2006) 343
3. Miller G.C., and Pritsos C.A. Cyanide: Soc., Ind. Econ. Aspects. Proc. Symp. Annu. Meet. TMS (2001) 73-81
4. Kulig K.W. Cyanide Toxicity (1991), U.S. Department of Health and Human Services, Atlanta, GA
5. Baskin S.L., and Brewer T.G. In: Sidell F.R., Takafuji E.T., and Franz D.R. (Eds). Medical Aspects of Chemical and Biological Warfare (1997), TMM Publications, Washington, DC 271-286
6. Baird C., and Cann M. Environmental Chemistry (2005), Freeman, New York
7. Lou X., Zhang L., Qin J., and Li Z. An alternative approach to develop a highly sensitive and selective chemosensor for the colorimetric sensing of cyanide in water. Chem. Commun. 44 (2008) 5848
8. Männel-Croisé C., and Zelder F. Side chains of cobalt corrinoids control the sensitivity and selectivity in the colorimetric detection of cyanide. Inorg. Chem. 48 (2009) 1272
9. Shang L., and Dong S. Design of fluorescent assays for cyanide and hydrogen peroxide based on the inner filter effect of metal nanoparticles. Anal. Chem. 81 (2009) 1465
10. Badugu R., Lakowicz J.R., and Geddes C.D. Enhanced fluorescence cyanide detection at physiologically lethal levels: reduced ict-based signal transduction. J. Am. Chem. Soc. 127 (2005) 3635
11. Kim Y., Zhao H., and Gabbaϊ F.P. Sulfonium boranes for the selective capture of cyanide ions in water. Angew. Chem. Int. Ed. 48 (2009) 4957
12. Touceda-Varela A., Stevenson E.I., Galve-Gasión J.A., Dryden D.T.F., and Mareque-Rivas J.C. Selective turn-on fluorescence detection of cyanide in water using hydrophobic CdSe quantum dots. Chem. Commun. 17 (2008) 1998
13. Sun S.S., and Lees A. J. Anion recognition through hydrogen bonding: a simple, yet highly sensitive, luminescent metal-complex receptor. Chem. Commun. 17 (2000) 1687
14. Miyaji H., and Sessler J.L. Off-the-shelf colorimetric anion sensors. Angew. Chem. Int. Ed. 40 (2001) 154
15. 3 surfaces. Chem. Eur. J. 14 (2008) 3006
16. Anzenbacher Jr. P., Tyson D.S., Jursíková K., and Castellano F.N. Luminescence lifetime-based sensor for cyanide and related anions. J. Am. Chem. Soc. 124 (2002) 6232
17. Tomasulo M., and Raymo F.M. Colorimetric detection of cyanide with a chromogenic oxazine. Org. Lett. 7 (2005) 4633
18. Tomasulo M., Sortino S., White A.J.P., and Raymo F.M. Chromogenic oxazines for cyanide detection. J. Org. Chem. 71 (2006) 744
19. García F., García J.M., García-Acosta B., Martínez-Máñez R., Sancenón F., and Soto J. Pyrylium-containing polymers as sensory materials for the colorimetric sensing of cyanide in water. Chem. Commun. 22 (2005) 2790
20. Ros-Lis J.V., Martínez-Máñez R., and Soto J. A selective chromogenic reagent for cyanide determination. Chem. Commun. 19 (2002) 2248
21. Lee H., Chung Y.M., and Ahn K.H. Selective fluorescence sensing of cyanide with an o-(carboxamido) trifluoroacetophenone fused with a cyano-1,2-diphenylethlene fluorophore. Tetrahedron Lett. 49 (2008) 5544
22. Miyaji H., Kim D.-S., Chang B.-Y., Park E., Park S.-M., and Ahn K.H. High cooperative ion-pair recognition of potassium cyanide using a heteroditopic ferrocene-based crown ether-trifluoroacetylcarboxanilide receptor. Chem. Commun. 6 (2008) 753
23. Chung Y., Lee H., and Ahn K.H. N-Acyl triazenes as tunable and selective chemodosimeters toward cyanide ion. J. Org. Chem. 71 (2006) 9470
24. Yang Y.-K., and Tae J. Acridinium salt based fluorescent and colorimetric chemosensor for the detection of cyanide in water. Org. Lett. 8 (2006) 5721
25. Lee K.-S., Lee J.T., Hong J.-I., and Kim H.-J. Visual detection of cyanide through intramolecular hydrogen bond. Chem. Lett. 36 (2007) 816
26. Lee K.-S., Kim H.-J., Kim G.-H., Shin I., and Hong J.-I. Fluorescent chemodosimeter for selective detection of cyanide in water. Org. Lett. 10 (2008) 49
27. Chen C.-L., Chen Y.-H., Chen C.-Y., and Sun S.-S. Dipyrrole carboxamide derived selective ratiometric probes for cyanide ion. Org. Lett. 8 (2006) 5053
28. Niu H.-T., Jiang X., He J., and Cheng J.-P. A highly selective and synthetically facile aqueous-phase cyanide probe. Tetrahedron Lett. 49 (2008) 6521
29. Sun Y., Wang G., and Guo W. Colorimetric detection of cyanide with N-nitrophenyl benzamide derivatives. Tetrahedron 65 (2009) 3480
30. Niu H.-T., Su D., Jiang X., Yang W., Yin Z., He J., and Cheng J.-P. A simple yet highly selective colorimetric sensor for cyanide anion in an aqueous environment. Org. Biomol. Chem. 6 (2008) 3038
31. Albayrak C., Odabasoglu M., Büyükgüngör O., and Lönnecke P. 5-(2-Chloro-phenyldiazenyl) salicylaldehyde and 4-(2-chlorophenyldiazenyl)-2-{[tris-(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one. Acta Crystallogr. 60 (2004) 318
32. Liu Y., Wang H., Wang L.-H., Li Z., Zhang H.-Y., and Zhang O. Synthesis of novel p-tert-butyl-calix[4]arene derivatives and their cation binding ability: chromogenic effect upon side arms binding. Tetrahedron 59 (2003) 7967
33. Braun D., Rettig W., Delmond S., Létard J.F., and Lapouyade R. Amide derivatives of DMABN: a new class of dual fluorescent compounds. J. Phys. Chem. A 101 (1997) 6836
34. Wu F.-Y., and Jiang Y.-B. p-Dimethylaminobenzamide as an ICT dual fluorescent neutral receptor for anions under proton coupled electron transfer sensing mechanism. Chem. Phys. Lett. 355 (2002) 438
35. 2+. Chem. Commun. 1 (2006) 106
36. Prasanna de Silva A., Nimal Gunaratne H.Q., Gunniaugsson T., Huxiey A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97 (1997) 1515
37. Watanabe S., Onogawa O., Komatsu Y., and Yoshida K. Luminescent metalloreceptor with a neutral bis(acylaminoidazoline) binding site: optical sensing of anionic and neural phosphodiesters. J. Am. Chem. Soc. 120 (1998) 229
38. Lee D.H., Im J.H., Lee J.-H., and Hong J.-I. A new fluorescent fluoride chemosensor based on conformational restriction of a biaryl fluorophore. Tetrahedron Lett. 43 (2002) 9637
39. Chung Y.M., Raman B., Kim D.-S., and Ahn K.H. Fluorescence modulation in anion sensing by introducing intramolecular H-bonding interactions in host-guest adducts. Chem. Commun. 2 (2006) 186
40. Ryu D., Park E., Kim D.-S., Yan S., Lee J.Y., Chang B.-Y., and Ahn K.H. A rational approach to fluorescence turn-on sensing of α-amino-carboxylates. J. Am. Chem. Soc. 130 (2008) 2094