Azo dyes featuring a pyrene unit: New selective chromogenic and fluorogenic chemodosimeters for Hg(II)

Sensors and Actuators, B: Chemical

Volumn 142, Issue 1, 2009, Pages 280-287

  Cheng, Chang Chiang ^a   Chen, Zhong Shin ^a   Wu, Chen Yu ^a   Lin, Chiung Cheng ^a   Yang, Chi Rei ^b   Yen, Yao Pin ^a  

^a PROVIDENCE UNIVERSITY   (Taiwan)

^b TAICHUNG VETERANS GENERAL HOSPITAL   (Taiwan)

Author keywords

Azo dyes; Chemodosimeters; Chromogenic sensor; Fluorogenic sensor; Mercury ion; Pyrene

Indexed keywords

AQUEOUS SOLUTIONS; CHEMODOSIMETERS; COLOR CHANGES; FLUORESCENCE ENHANCEMENT; FLUOROGENIC SENSOR; FLUOROGENICS; MERCURY ION; METAL CATION; TEST STRIPS;

AZO DYES; CHROMOGENICS; COLORIMETRY; DIMETHYL SULFOXIDE; FLUORESCENCE; POSITIVE IONS; SENSORS;

MERCURY (METAL);

EID: 70349243076     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2009.07.020     Document Type: Article

References (55)

1. Czarnik A.W. Fluorescent Chemosensors for Ion and Molecule Recognition (1993), American Chemical Society, Washington, DC
2. de Silva A.P., Fox D.B., Huxley A.J.M., and Moody T.S. Combining luminescence, coordination and electron transfer for signaling purposes. Chem. Rev. 205 (2000) 41-57
3. 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 (1997) 1515-1566
4. Desvergne J.P., and Czarnik A.W. Chemosensors of Ion and Molecule Recognition (1997), Kluwer, Dordrecht
5. Tchounwou P.B., Ayensu W.K., Ninashvili N., and Sutton D. Environmental exposure to mercury and its toxicopathologic implications for public health. Environ. Toxicol. 18 (2003) 149-175
6. Grandjean P., Weihe P., White R.F., and Debes F. Cognitive performance of children prenatally exposed to "Safe" levels of methylmercury. Environ. Res. 77 (1998) 165-172
7. Takeuchi T., Morikawa N., Matsumoto H., and Shiraishi Y. A pathological study of Minamata disease in Japan. Acta Neuropathol. 2 (1962) 40-57
8. Harada M. Minamata disease: methylmercury poisoning in Japan caused by environmental pollution. Crit. Rev. Toxicol. 25 (1995) 1-24
9. Coskun A., Yilmaz M.D., and Akkaya E.U. Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II). Org. Lett. 9 (2007) 607-609
10. 2+ based on the rhodamine fluorophore. Org. Lett. 9 (2007) 2501-2504
11. 2+ ion binding with high sensitivity. Org. Lett. 8 (2006) 3721-3724
12. Yoon S., Albers A.E., Wong A., and Chang C.J. Screening mercury levels in fish with a selective fluorescent chemosensor. J. Am. Chem. Soc. 127 (2005) 16030-16031
13. 2+ in neutral buffer aqueous solution. J. Am. Chem. Soc. 126 (2004) 2272-2273
14. Nolan E.M., and Lippard S.J. A "Turn-On" fluorescent sensor for the selective detection of mercuric ion in aqueous media. J. Am. Chem. Soc. 125 (2003) 14270-14271
15. Zhu X., Fu S., Wong W., Guo J., and Wong W. A near-infrared-fluorescent chemodosimeter for mercuric ion based on an expanded porphyrin. Angew. Chem. Int. Ed. 45 (2006) 3150-3154
16. Nolan E.M., and Lippard S.J. Tools and tactics for the optical detection of mercuric ion. Chem. Rev. 108 (2008) 3443-3480
17. Manimala J.C., and Anslyn E.V. Solid-phase synthesis of guanidinium derivatives from thiourea and isothiourea functionalities. Eur. J. Org. Chem. (2002) 3909-3922
18. Kim K.S., and Qian L. Improved method for the preparation of guanidines. Tetrahedron Lett. 34 (1993) 7677-7680
19. Batey R.A., and Powell D.A. A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: a strategy for diversity amplification. Org. Lett. 2 (2000) 3237-3240
20. Boeglin D., Cantel S., Heitz A., Martinez J., and Fehrentz J.A. Solution and solid-supported synthesis of 3,4,5-trisubstituted 1,2,4-triazole-based peptidomimetics. Org. Lett 5 (2003) 4465-4468
21. Chae M.-Y., and Czarnik A.W. Fluorimetric chemodosimetry. Mercury(II) and Silver(I) indication in water via enhanced fluorescence signaling. J. Am. Chem. Soc. 144 (1992) 9704-9706
22. Hennrich G., Walther W., Resch-Genger U., and Sonnenschein H. Cu(II)- and Hg(II)-induced modulation of the fluorescence behavior of a redox-active sensor molecule. Inorg. Chem. 40 (2001) 641-644
23. 2+-aelective chemodosimeter derived from 8-hydroxyquinoline. Org. Lett. 8 (2006) 3413-3416
24. Liu B., and Tian H. A selective fluorescent ratiometric chemodosimeter for mercury ion. Chem. Commun. (2005) 3156-3158
25. 2+ ions in aqueous media. J. Am. Chem. Soc. 127 (2005) 16760-16761
26. Ko S.-K., Yang Y.-K., Tae J., and Shin I. In vivo monitoring of mercury ions using a rhodamine-based molecular probe. J. Am. Chem. Soc. 128 (2006) 14150-14155
27. 2+-selective chemodosimeter in aqueous solution: fluorescent OFF-ON. Org. Lett. 9 (2007) 907-910
28. 2+ ions. Angew. Chem. Int. Ed. 44 (2005) 4405-4407
29. Martinez-manez R., and Sancenon F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 103 (2003) 4419-4476
30. Lee M.H., Cho B.-K., Yoon J., and Kim J.S. Selectively chemodosimetric detection of Hg(II) in aqueous media. Org. Lett. 9 (2007) 4515-4518
31. 2+ in aqueous environment based on 1,4-disubstituted azines. J. Am. Chem. Soc. 127 (2005) 15666-15667
32. Oton F., Espinosa A., Tarraga A., Ratera I., Wurst K., Veciana J., and Molina P. Mononuclear ferrocenophane structural motifs with two thiourea arms acting as a dual binding site for anions and cations. Inorg. Chem. 48 (2009) 1566-1576
33. 2+-selective signaling by mercuration of dichlorofluorescein derivatives. Org. Lett. 10 (2008) 3717-3720
34. Winnik F.M. Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media. Chem. Rev. 93 (1993) 587-614
35. Kim J.S., Noh K.H., Lee S.H., Kim S.K., and Yoon J. Molecular taekwondo. 2. A new calix[4]azacrown bearing two different binding sites as a new fluorescent ionophore. J. Org. Chem 68 (2003) 597-600
36. Yuasa H., Miyagawa N., Izumi T., Nakatani M., Izumi M., and Hashimoto H. Hinge sugar as a movable component of an excimer fluorescence sensor. Org. Lett. 6 (2004) 1489-1492
37. Yu B.-C., Shirai Y., and Tour J.M. Syntheses of new functionalized azobenzenes for potential molecular electronic devices. Tetrahedron 62 (2006) 10303-10310
38. 3S = 307.0392.
39. Martvon A., Antos K., and Sticzay T. Synthesis, infrared and ultraviolet spectra of isothiocyanatoazobenzenes. Collect. Czech. Chem. Commun. 34 (1969) 3912-3920
40. 3O = 291.0620.
41. Cho E.J., Ryu B.J., Lee Y.J., and Nam K.C. Visible colorimetric fluoride ion sensors. Org. Lett. 7 (2005) 2607-2609
42. Koevoets R.A., Versteegen R.M., Kooijman H., Spek A.L., Sijbesma R.P., and Meijer E.W. Molecular recognition in a thermoplastic elastomer. J. Am. Chem. Soc. 127 (2005) 2999-3003
43. Masse C.E., Wiede K.V., Kim W.H., Jiang X.L., and Tripathy S.K. Novel unsymmetrical polydiacetylenes as materials for second- and third-order nonlinear optics. Chem. Mater. 7 (1995) 904-908
44. Raiford L.C., and Freyermuth H.B. Formation and properties of some uretediones. J. Org. Chem. 3 (1943) 230-238
45. Corsaro A., and Pistara V. Conversion of the thiocarbonyl group into the carbonyl group. Tetrahedron 54 (1998) 15027-15062
46. Ono A., and Togashi H. Highly selective oligonucleotide-based sensor for mercury(II) in aqueous solutions. Angew. Chem. Int. Ed. 43 (2004) 4300-4302. Detection limit is defined by 3σ/K. Here σ and K refer to the standard deviation of the blank solutions and the slope (σ) of the linear regression curve observed in Fig. 6b, respectively.
47. Liu J., and Lu Y. Rational design of "Turn-On" allosteric DNAzyme catalytic beacons for aqueous mercury ions with ultra high sensitivity and selectivity. Angew. Chem. Int. Ed. 46 (2007) 7587-7590
48. 2+ selective chromo and fluoroionophore based on a bichromophoric azine. Org. Lett. 7 (2005) 5869-5872
49. 2+-selective ON-OFF type fluoroionophore based upon cyclam. Org. Lett. 8 (2006) 371-374
50. Yoon J., Ohler N.E., Vance D.H., Aumiller W.D., and Czarnik A.W. A fluorescent chemosensor signaling only Hg(II) and Cu(II) in water. Tetrahedron Lett. 38 (1997) 3845-3848
51. Feng K., Hsu F.-L., Bota K., and Bu X.R. A potential fluorescent Hg(II) chemosensor. Microchem. J. 81 (2005) 23-27
52. Dawson W.R., and Windsor M.W. Fluorescence yields of aromatic compounds. J. Phys. Chem. 72 (1968) 3251-3260. The fluorescence quantum yields were measured with respect to anthracene as standard (Φ = 0.27 ± 0.03).
53. Coronado E., Galan-Mascaros J.R., Marti-Gastaldo G., Palomares E., Durrant J.R., Vilar R., Gratzel M., and Nazeeruddin Md.K. Reversible colorimetric probes for mercury sensing. J. Am. Chem. Soc. 127 (2005) 12351-12356
54. Polomares E., Vilar R., and Durrant J.R. Heterogeneous colorimetric sensor for mercury salts. Chem. Commun. (2004) 362-363
55. Tatay S., Gavina P., Coronado E., and Polomares E. Optical mercury sensing using a benzothiazolium hemicyanine dye. Org. Lett. 8 (2006) 3857-3860