Dansyl-containing fluorogenic calixarenes as optical chemosensors of hazardous metal ions: A mini-review

Supramolecular Chemistry

Volumn 22, Issue 11-12, 2010, Pages 838-852

  Talanova, Galina G ^a   Talanov, Vladimir S ^a  

^a HOWARD UNIVERSITY   (United States)

Author keywords

chemosensors; dansyl; fluorogenic calixarenes; heavy metal ions; optical recognition

Indexed keywords

EID: 78649491480     PISSN: 10610278     EISSN: 10290478     Source Type: Journal    
DOI: 10.1080/10610278.2010.514612     Document Type: Article

References (69)

1. US Environmental Protection Agency, National Primary Drinking Water Standards, Report EPA, 816-F-09-004, 2009.
2. World Health Organization, Guidelines for Drinking-Water Quality, 3rd ed. Geneva, 2004; Vol. 1.
3. de Silva, 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.
4. Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780-3799.
5. Valeur, B.; Leray, I. Inorg. Chim. Acta 2007, 360, 765-774.
6. Leray, I.; Valeur, B. Eur. J. Inorg. Chem. 2009, 3525-3535.
7. Tolosa, L.; Nowaczyk, K.; Lakowicz, J. Fluorescence Probes for Biochemical Systems. In Introduction to Laser Spectroscopy; Andrews, D. L., Demidov, A. A., Eds.; Kluwer Academic/Plenum Publishers: New York, 2002; pp 139-170.
8. Shreder, K. Methods 2000, 20, 372-379.
9. Bailey, M. F.; Thompson, E. H. Z.; Millar, D. P. Methods 2001, 25, 62-67.
10. Takeuchi, T. HPLC of Amino Acids as Dansyl and Dabsyl Derivatives. In Journal of Chromatography Library. v. 70 Quantitation of Amino Acids and Amines by Chromatography - Methods and Protocols; Molnar-Perl, I., Ed.; Elsevier: Amsterdam, 2005; pp 229-241.
11. Silva, M. Quantitation by HPLC of Amines as Dansyl Derivatives. In Journal of Chromatography Library. v. 70 Quantitation of Amino Acids and Amines by Chromatography - Methods and Protocols; Molnar-Perl, I., Ed.; Elsevier: Amsterdam, 2005; pp 445-470.
12. Ueno, A. Supramol. Sci. 1996, 3, 31-36.
13. Nelissen, H. F. M.; Venema, F.; Uittenbogaard, R. M.; Feiters, M. C.; Nolte, R. J. M. J. Chem. Soc., Perkin Trans. 2 1997, 2045-2053.
14. Bugler, J.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1998, 63, 5339-5344.
15. de Jong, M. R.; Engbersen, J. F. J.; Huskens, J.; Reinhoudt, D. N. Chem. Eur. J. 2000, 6, 4034-4040.
16. Schuster, M.; Sandor, M. Fresenius J. Anal. Chem. 1996, 356, 326-330.
17. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Eur. J. Inorg. Chem. 1999, 455-460.
18. Kavallieratos, K.; Rosenberg, J. M.; Chen, W. Z.; Ren, T. J. Am. Chem. Soc. 2005, 127, 6514-6515.
19. Jisha, V. S.; Thomas, A. J.; Ramaiah, D. J. Org. Chem. 2009, 74, 6667-6673.
20. Wu, H.; Zhou, P.; Wang, J.; Zhao, L.; Duan, C. New J. Chem. 2009, 33, 653-658.
21. Kimura, E.; Koike, T. Chem. Soc. Rev. 1998, 27, 179-184.
22. Aoki, S.; Kawatani, H.; Goto, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 2001, 123, 1123-1132.
23. Lowe, M. P.; Parker, D. Inorg. Chim. Acta 2001, 317, 163-173.
24. Fabbrizzi, L.; Foti, F.; Licchelli, M.; Maccarini, P. M.; Sacchi, D.; Zema, M. Chem. Eur. J. 2002, 8, 4965-4972.
25. Blake, A. J.; Bencini, A.; Caltagirone, C.; De Filippo, G.; Dolci, L. S.; Garau, A.; Isaia, F.; Lippolis, V.; Mariani, P.; Prodi, L.; Montalti, M.; Zaccheroni, N.; Wilson, C. Dalton Trans. 2004, 2771-2779.
26. Rivero, I. A.; Gonzalez, T.; Pina-Luis, G.; Diaz-Garcia, M. E. J. Comb. Chem. 2005, 7, 46-53.
27. White, B. R.; Liljestrand, H. M.; Holcombe, J. A. Analyst 2008, 133, 65-70.
28. Joshi, B. P.; Lee, K.-H. Bioorg. Med. Chem. 2008, 16, 8501-8509.
29. Ma, L.-J.; Li, Y.; Li, L.; Sun, J.; Tian, C.; Wu, Y. Chem. Commun. 2008, 6345-6347.
30. Crego-Calama, M.; Reinhoudt, D. N. Adv. Mater. 2001, 13, 1071-1074.
31. Rampazzo, E.; Brazola, E.; Marcuz, S.; Mancin, F.; Tecilla, P.; Tonellato, U. J. Mater. Chem. 2005, 15, 2687-2696.
32. Arduini, M.; Mancin, F.; Tecilla, P.; Tonelatto, U. Langmuir 2007, 23, 8632-8636.
33. Mu, L.; Shi, W.; She, G.; Chang, J. C.; Lee, S.-T. Angew. Chem., Int. Ed. 2009, 48, 3469-3472.
34. Branchi, B.; Ceroni, P.; Balzani, V.; Bergamini, G.; Klarner, F.-G.; Vogtle, F. Chem. Eur. J. 2009, 15, 7876-7882.
35. Yin, J.; Guan, X.; Wang, D.; Liu, S. Langmuir 2009, 25, 11367-11374.
36. Narita, M.; Higuchi, Y.; Hamada, F.; Kumagai, H. Tetrahedron Lett. 1998, 39, 8687-8690.
37. Talanova, G. G.; Elkarim, N. S. A.; Talanov, V. S.; Bartsch, R. A. Anal. Chem. 1999, 71, 3106-3109.
38. Schönefeld, K.; Ludwig, R.; Feller, K.-H. J. Fluoresc. 2006, 16, 449-454.
39. Miao, R.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Tetrahedron Lett. 2004, 45, 4959-4962.
40. Liu, S.-Y.; He, Y.-B.; Qing, G.-Y.; Xu, K.-X.; Qin, H.-J. Tetrahedron: Asymmetry 2005, 16, 1527-1534.
41. Métivier, R.; Leray, I.; Valeur, B. J. Mater. Chem. 2005, 15, 2965-2973.
42. Dinake, P.; Prokhorova, P. E.; Talanov, V. S.; Butcher, R. J.; Talanova, G. G. Tetrahedron Lett. 2010, 51, 5016-5019.
43. Métivier, R.; Leray, I.; Valeur, B. Chem. Commun. 2003, 996-997.
44. Buie, N. M.; Talanov, V. S.; Butcher, R. J.; Talanova, G. G. Inorg. Chem. 2008, 47, 3549-3558.
45. Ocak, U.; Ocak, M.; Surowiec, K.; Bartsch, R. A.; Gorbunova, M. G.; Tu, G.; Surowiec, M. A. J. Incl. Phenom. Macrocycl. Chem. 2009, 63, 131-139.
46. Ocak, U.; Ocak, M.; Surowiec, K.; Liu, X.; Bartsch, R. A. Tetrahedron 2009, 65, 7038-7047.
47. Ocak, U.; Ocak, M.; Shen, X.; Surowiec, K.; Bartsch, R. A. J. Fluoresc. 2009, 19, 997-1008.
48. Talanova, G. G.; Roper, E. D.; Buie, N. M.; Gorbunova, M. G.; Bartsch, R. A.; Talanov, V. S. Chem. Commun. 2005, 5673-5675.
49. Talanov, V. S.; Roper, E. D.; Buie, N. M.; Talanova, G. G. Tetrahedron Lett. 2007, 48, 8022-8025.
50. Goretzki, G.; Bonnesen, P. V.; Dabestani, R.; Brown, G. M. Fluorophores as Chemosensors Based on Calix[4]arenes and Three Different Fluorescence Reporters. In Nuclear Waste Management: Wang, P. W., Zachry, T., Eds.; ACS Symposium Series 943; American Chemical Society: Washington, DC, 2006; Chapter 2, pp 12-33.
51. Chen, Q.-Y.; Chen, C.-F. Tetrahedron Lett. 2005, 46, 165-168.
52. Dhir, A.; Bhalla, V.; Kumar, M. Org. Lett. 2008, 10, 4891-4894.
53. Li, G.-K.; Liu, M.; Yang, J.-Q.; Chen, C.-F.; Huang, Z.-T. Chinese J. Chem. 2008, 26, 1440-1446.
54. Bhalla, V.; Kumar, R.; Kumar, M.; Dhir, A. Tetrahedron 2007, 63, 11153-11159.
55. Pandey, S.; Azam, A.; Pandey, S.; Chawla, H. M. Org. Biomol. Chem. 2009, 7, 269-279.
56. Gruber, T.; Fischer, C.; Felsmann, M.; Seichter, W.; Weber, E. Org. Biomol. Chem. 2009, 7, 4904-4917.
57. Higuchi, Y.; Narita, M.; Niimi, T.; Ogawa, N.; Hamada, F.; Kumagai, H.; Iki, N.; Miyano, S.; Kabuto, C. Tetrahedron 2000, 56, 4659-4666.
58. Roper, E. D.; Talanov, V. S.; Gorbunova, M. G.; Bartsch, R. A.; Talanova, G. G. Anal. Chem. 2007, 79, 1983-1989.
59. Lhotak, P. Eur. J. Org. Chem. 2004, 1675-1692.
60. Long, G. L.; Winefordner, J. D. Anal. Chem. 1983, 55, 712A-714A.
61. Valeur, B. Molecular Fluorescence. Principles and Applications; Wiley-VCH: Weinheim, 2002; pp 339-348.
62. Métivier, R.; Leray, I.; Valeur, B. Chem. Eur. J. 2004, 10, 4480-4490.
63. Montgomery, J. A.; Thomas, H. J. J. Org. Chem. 1966, 31, 1411-1413.
64. Talanov, V. S.; Hwang, H.-S.; Bartsch, R. A. J. Chem. Soc. Perkin Trans. 2 2001, 1103-1108.
65. Talanova, G. G.; Talanov, V. S.; Hwang, H.-S.; Park, C.; Surowiec, K.; Bartsch, R. A. Org. Biomol. Chem. 2004, 2, 2585-2592.
66. Zhao, L.; Wu, T.; Lefevre, J.-P.; Leray, I.; Delaire, J. A. Lab Chip 2009, 9, 2818-2823.
67. Asfari, Z.; Naumann, C.; Vicens, J.; Nierlich, M.; Thuery, P.; Bressot, C.; Lamare, V.; Dozol, J.-F. New J. Chem. 1996, 20, 1183-1194.
68. Talanov, V. S.; Talanova, G. G.; Gorbunova, M. G.; Bartsch, R. A. J. Chem. Soc. Perkin Trans. 2 2002, 209-215.
69. Gutsche, C. D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1998.