A click fluorophore sensor that can distinguish CuII and Hg II via selective anion-induced demetallation

Chemistry - A European Journal

Volumn 17, Issue 10, 2011, Pages 2850-2858

  Lau, Yu Heng ^a   Price, Jason R ^a   Todd, Matthew H ^a   Rutledge, Peter J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

anions; azamacrocycles; chemosensors; click chemistry; fluorescence

Indexed keywords

ANIONS; AZA MACROCYCLES; CHEMO-SENSORS; CLICK CHEMISTRY; COORDINATION MODES; DEMETALLATION; FLUORESCENT SENSORS; MACROCYCLES; NEUTRAL AQUEOUS SOLUTION; NITROGEN ATOM; SEAWATER SAMPLES; X RAY CRYSTAL STRUCTURES;

COORDINATION REACTIONS; DOPING (ADDITIVES); FLUORESCENCE; MASS SPECTROMETRY; METAL IONS; NEGATIVE IONS; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEAWATER; SENSORS;

MERCURY (METAL);

ANION; COPPER; CYCLAM; DIAGNOSTIC AGENT; FLUORESCENT DYE; HEAVY METAL; HETEROCYCLIC COMPOUND; MERCURY; TRIAZOLE DERIVATIVE; WATER; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY; SYNTHESIS;

ANIONS; CLICK CHEMISTRY; COPPER; FLUORESCENT DYES; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MERCURY; METALS, HEAVY; MOLECULAR STRUCTURE; SOLUTIONS; TRIAZOLES; WATER; ZINC;

EID: 79951981377     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002477     Document Type: Article

References (65)

1. L. Basabe-Desmonts, D. N. Reinhoudt, M. Crego-Calama, Chem. Soc. Rev. 2007, 36, 993-1017
2. K. Kikuchi, Chem. Soc. Rev. 2010, 39, 2048-2053
3. Fluorescent Chemosensors for Ion and Molecule Recognition (Ed.:, A. W. Czarnik,), American Chemical Society, Washington DC, 1993
4. P. Lieberzeit, F. Dickert, Anal. Bioanal. Chem. 2009, 393, 467-472
5. O. S. Wolfbeis, J. Mater. Chem. 2005, 15, 2657-2669.
6. For recent reviews see
7. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515-1566
8. M. Kruppa, B. König, Chem. Rev. 2006, 106, 3520-3560
9. R. Martínez-Máñez, F. Sancenón, Chem. Rev. 2003, 103, 4419-4476
10. E. Pazos, O. Vázquez, J. L. Mascareñas, M. E. Vázquez, Chem. Soc. Rev. 2009, 38, 3348-3359
11. T. D. James, S. Shinkai, Top. Curr. Chem. 2002, 218, 159-200
12. T. W. Bell, N. M. Hext, Chem. Soc. Rev. 2004, 33, 589-598
13. J. F. Callan, A. P. de Silva, D. C. Magri, Tetrahedron 2005, 61, 8551-8588
14. B. Valeur, I. Leray, Coord. Chem. Rev. 2000, 205, 3-40
15. E. V. Anslyn, J. Org. Chem. 2007, 72, 687-699
16. B. T. Nguyen, E. V. Anslyn, Coord. Chem. Rev. 2006, 250, 3118-3127
17. E. M. Nolan, S. J. Lippard, Chem. Rev. 2008, 108, 3443-3480.
18. L. Fabbrizzi, A. Poggi, Chem. Soc. Rev. 1995, 24, 197-202.
19. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
20. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
21. H. Struthers, T. L. Mindt, R. Schibli, Dalton Trans. 2010, 39, 675-696
22. M. Meldal, Chem. Rev. 2008, 108, 2952-3015.
23. T. L. Mindt, H. Struthers, L. Brans, T. Anguelov, C. Schweinsberg, V. Maes, D. Tourwé, R. Schibli, J. Am. Chem. Soc. 2006, 128, 15096-15097.
24. CSD version 5.31 with updates (May 2010). See also a recent paper containing a literature search of N2 coordination:, D. Urankar, B. Pinter, A. Pevec, F. De Proft, I. Turel, J. Koámrlj, Inorg. Chem. 2010, 49, 4820-4829.
25. E. Tamanini, A. Katewa, L. M. Sedger, M. H. Todd, M. Watkinson, Inorg. Chem. 2009, 48, 319-324.
26. E. Tamanini, K. Flavin, M. Motevalli, S. Piperno, L. A. Gheber, M. H. Todd, M. Watkinson, Inorg. Chem. 2010, 49, 3789-3800.
27. E. Tamanini, S. E. Rigby, M. Motevalli, M. H. Todd, M. Watkinson, Chem. Eur. J. 2009, 15, 3720-3728.
28. D. J. Waggoner, T. B. Bartnikas, J. D. Gitlin, Neurobiol. Dis. 1999, 6, 221-230.
29. P. Grandjean, P. Weihe, R. F. White, F. Debes, Environ. Res. 1998, 77, 165-172
30. M. Harada, Crit. Rev. Toxicol. 1995, 25, 1-24
31. D. W. Boening, Chemosphere 2000, 40, 1335-1351
32. T. W. Clarkson, L. Magos, G. J. Myers, N. Engl. J. Med. 2003, 349, 1731-1737.
33. S.-Y. Moon, N. J. Youn, S. M. Park, S.-K. Chang, J. Org. Chem. 2005, 70, 2394-2397
34. S. H. Kim, J. S. Kim, S. M. Park, S.-K. Chang, Org. Lett. 2006, 8, 371-374
35. Y. Al Shihadeh, A. Benito, J. M. Lloris, R. Martínez- Máñez, T. Pardo, J. Soto, M. D. Marcos, J. Chem. Soc. Dalton Trans. 2000, 1199-1205
36. K.-C. Song, M. H. Kim, H. J. Kim, S.-K. Chang, Tetrahedron Lett. 2007, 48, 7464-7468
37. S. M. Park, M. H. Kim, J.-I. Choe, K. T. No, S.-K. Chang, J. Org. Chem. 2007, 72, 3550-3553.
38. P. Qin, C. Niu, G. Zeng, J. Zhu, L. Yue, Anal. Sci. 2008, 24, 1205-1208
39. Y.-C. Hsieh, J.-L. Chir, H.-H. Wu, P.-S. Chang, A.-T. Wu, Carbohydr. Res. 2009, 344, 2236-2239
40. Y.-B. Chen, Y.-J. Wang, Y.-J. Lin, C.-H. Hu, S.-J. Chen, J.-L. Chir, A.-T. Wu, Carbohydr. Res. 2010, 345, 956-959.
41. S. J. Krivickas, E. Tamanini, M. H. Todd, M. Watkinson, J. Org. Chem. 2007, 72, 8280-8289.
42. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
43. H. Masuhara, H. Shioyama, T. Saito, K. Hamada, S. Yasoshima, N. Mataga, J. Phys. Chem. 1984, 88, 5868-5873
44. M. D. P. De Costa, W. A. P. A. Jayasinghe, J. Photochem. Photobiol. A 2004, 162, 591-598
45. D. S. McClure, J. Chem. Phys. 1952, 20, 682-686
46. A. W. Varnes, R. B. Dodson, E. L. Wehry, J. Am. Chem. Soc. 1972, 94, 946-950.
47. K. A. Connors, Binding Constants: The Measurement of Molecular Complex Stability, Wiley, New York, 1987.
48. Using 5 standard deviations, following the definition from the Gold Book:, A. D. McNaught, A. Wilkinson, in IUPAC Compendium of Chemical Terminology, 2 nd ed., Blackwell Scientific Publications, Oxford, 1997.
49. A. P. de Silva, T. S. Moody, G. D. Wright, Analyst 2009, 134, 2385-2393.
50. L. F. Lindoy, in The Chemistry of Macrocyclic Ligand Complexes, Cambridge University Press, Cambridge, 1989.
51. S. Mizukami, T. Nagano, Y. Urano, A. Odani, K. Kikuchi, J. Am. Chem. Soc. 2002, 124, 3920-3925
52. Z. Wu, Y. Zhang, J. S. Ma, G. Yang, Inorg. Chem. 2006, 45, 3140-3142
53. G. He, Y. Zhao, C. He, Y. Liu, C. Duan, Inorg. Chem. 2008, 47, 5169-5176
54. II removal, exo coordination of the metal is possible, although the experiments conducted showed no evidence of this coordination mode. See
55. J. Du, J. Fan, X. Peng, H. Li, J. Wang, S. Sun, J. Fluoresc. 2008, 18, 919-924
56. S. J. Lee, J. H. Jung, J. Seo, I. Yoon, K.-M. Park, L. F. Lindoy, S. S. Lee, Org. Lett. 2006, 8, 1641-1643
57. H. J. Kim, S. S. Lee, Inorg. Chem. 2008, 47, 10807-10809. Redox effects were also considered, but since macrocycle coordination tends to stabilise higher oxidation states, the fluorescence revival is unlikely to be due to reduction at the metal centre by the anions introduced; see
58. L. Fabbrizzi, Comments Inorg. Chem. 1985, 4, 33-54.
59. J. G. Speight, Lange's Handbook of Chemistry, 16 th ed., McGraw-Hill, 2005, pp. 337.
60. C. J. Nyman, T. Salazar, Anal. Chem. 1961, 33, 1467-1469.
61. Z. P. Demko, K. B. Sharpless, Org. Lett. 2001, 3, 4091-4094.
62. T. Sugino, K. Tanaka, Chem. Lett. 2001, 110-111
63. D. R. Breed, R. Thibault, F. Xie, Q. Wang, C. J. Hawker, D. J. Pine, Langmuir 2009, 25, 4370-4376.
64. L. Fabbrizzi, F. Foti, M. Licchelli, P. M. Maccarini, D. Sacchi, M. Zema, Chem. Eur. J. 2002, 8, 4965-4972.
65. R. F. Chen, Anal. Lett. 1967, 1, 35-42.