Fluorescent phosphane selenide as efficient mercury chemodosimeter

Organic Letters

Volumn 13, Issue 5, 2011, Pages 1182-1185

  Samb, Issa ^a   Bell, Jérémy ^b   Toullec, Patrick Y ^a   Michelet, Véronique ^a   Leray, Isabelle ^b  

^a PSL RESEARCH UNIVERSITY   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIAGNOSTIC AGENT; FLUORESCENT DYE; MERCURY; ORGANOSELENIUM DERIVATIVE; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; POLLUTANT; SYNTHESIS; WORLD HEALTH ORGANIZATION;

ENVIRONMENTAL POLLUTANTS; FLUORESCENT DYES; MERCURY; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS; PHOSPHINES; WORLD HEALTH ORGANIZATION;

EID: 79952164202     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200066p     Document Type: Article

References (39)

1. Hutchinson, T. C.; Meena, K. M. In Lead, Mercury, Cadmium and Arsenic in the Environment; John Wiley: New York, 1987.
2. Scoullos, G. H.; Vonkeman, M. J.; Thorton, L.; Makuch, Z. In Mercury, Cadmium, Lead: Handbook for Sustainable Heavy Metals Policy and Regulation (Environment and Policy, V. 31); Kluwer Academic: Norwell, MA, 2001.
3. Koester, C. J.; Moulik, A. Anal. Chem. 2005, 77, 3737-3754
4. Richardson, S. D.; Temes, T. A. Anal. Chem. 2005, 77, 3807-3838
5. Clarkson, T. W.; Magos, L.; Myers, G. J. N. Engl. J. Med. 2003, 349, 1731-1737
6. Carvalho, C. M. L.; Chew, E.-H.; Hashemy, S. I.; Lu, J.; Holmgren, A. J. Biol. Chem. 2008, 283, 11913
7. Guidelines for drinking-water quality, 3 rd ed.; World Health Organization: Geneva, 2004; p 188.
8. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3-40
9. Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443-3480
10. deSilva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566
11. Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443-3480
12. Leray, I.; Valeur, B. Eur. J. Inorg. Chem. 2009, 3525-3535
13. Melnik, J. G.; Yurkervich, K.; Parkin, G. J. Am. Chem. Soc. 2010, 132, 647-655
14. For selected examples of fluorescent chemodosensors exploiting the thiophilicity of mercury, see: J Ros-Lis, J. V.; Marcos, M. D.; Martinez-Manez, R.; Rurack, K.; Soto, J. Angew. Chem. 2005, 44, 4405-4407
15. Yang, Y.-K.; Yook, K.-J.; Tae J. Am. Chem. Soc. 2005, 127, 16760-16761
16. Liu, B.; Tian, H. Chem. Commun. 2005, 3156-3158
17. Song, K. C.; Kim, J. S.; Park, S. M.; Chung, K. C.; Ahn, S.; Chang, S. K. Org. Lett. 2006, 8, 3413-3416
18. Shi, W.; Ma, H. M. Chem. Commun. 2008, 1856-1858
19. Lee, M. H.; Lee, S. W.; Kim, S. H.; Kang, C.; Kim, J. S. Org. Lett. 2009, 11, 2101-2104
20. Tian, M. Q.; Ihmels, H. Chem. Commun. 2009, 3175-3177
21. Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030-16031
22. Lin, W. Y.; Cao, X. W.; Ding, Y. D.; Yuan, L.; Long, L. L. Chem. Commun. 2010, 46, 3529-3531
23. For two recent examples of fluorescent chemodosimeters exploiting the selenophilicity of mercury, see: Tang, B.; Ding, B.; Xu, K.; Tong, L. Chem.-Eur. J. 2009, 15, 3147-3151
24. Chen, X.; Baek, K.-H.; Kim, Y.; Kim, S.-J.; Shin, I.; Yoon, J. Tetrahedron 2010, 66, 4016-4021
25. Miksa, I. R.; Buckley, C. L.; Carpenter, N. P.; Poppenga, R. H. J. Vet. Diagn. Invest. 2005, 17, 331-340
26. Arai, T.; Ikemoto, T.; Hokura, A.; Terada, Y.; Kunito, T.; Tanabe, S.; Nakai, I. Environ. Sci. Technol. 2004, 38, 6468-6474
27. Ha-Thi, M. H.; Souchon, V.; Hamdi, A.; Metivier, R.; Alain, V.; Nakatani, K.; Lacroix, P. G.; Genet, J. P.; Michelet, V.; Leray, I. Chem.-Eur. J. 2006, 12, 9056-9065
28. Ha-Thi, M. H.; Penhoat, M.; Michelet, V.; Leray, I. Org. Lett. 2007, 9, 1133-1136
29. Ha-Thi, M. H.; Souchon, V.; Penhoat, M.; Miomandre, F.; Genet, J. P.; Leray, I.; Michelet, V. Lett. Org. Chem. 2007, 4, 185-188
30. Ha-Thi, M. H.; Penhoat, M.; Drouin, D.; Blanchard-Desce, M.; Michelet, V.; Leray, I. Chem.-Eur. J. 2008, 14, 5941-5950
31. Ha-Thi, M. H.; Penhoat, M.; Michelet, V.; Leray, I. Org. Biomol. Chem. 2009, 7, 1665-1673
32. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874-922
33. Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871
34. Hajduk, P. J.; Sheppard, G.; Nettesheim, D. G.; Olejniczak, E. T.; Shuker, S. B.; Meadows, R. P.; Steinman, D. H.; Carrera, G. M., Jr.; Marcotte, P. A.; Severin, J.; Walter, K.; Smith, H.; Gubbins, E.; Simmer, R.; Holzman, T. F.; Morgan, D. W.; Davidsen, S. K.; Summers, J. B.; Fesik, S. W. J. Am. Chem. Soc. 1997, 119, 5818-5827
35. MES: 2-(N -morpholino)ethanesulfonic acid.
36. Gulyas, H.; Bacsik, Z.; Szollosy, A.; Bakos, J. Adv. Synth. Catal. 2006, 348, 1306-1310 and references cited therein
37. Ye, B. C.; Yin, B. C. Angew. Chem., Int. Ed. 2008, 47, 8386-8389
38. Wegner, S. V.; Okesli, A.; Chen, P.; He, C. J. Am. Chem. Soc. 2007, 129, 3474-3475
39. Nolan, E. M.; Racine, M. E.; Lippard, S. J. Inorg. Chem. 2006, 45, 2742-2749