2-Aza-1,3-butadiene ligands for the selective detection of Hg2+ and Cu2+ ions

Arkivoc

Volumn 2010, Issue 3, 2010, Pages 124-144

  Martínez, Rosario ^a   Zapata, Fabiola ^a   Caballero, Antonio ^a   Espinosa, Arturo ^a   Tárraga, Alberto ^a   Molina, Pedro ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

2 aza 1,3 butadiene; Chromogenic chemosensors; Cu2+; Fluorescent chemosensors; Hg2+; Redox

Indexed keywords

EID: 84962460164     PISSN: 15517012     EISSN: 15517004     Source Type: None    
DOI: 10.3998/ark.5550190.0011.312     Document Type: Article

References (74)

1. (a) Chemosensors of Ions and Molecular Recognitions; Desvergne, J. P.; Czarnik, A. W. Eds.; NATO ASI Series, Kluwer Academic: Dordrecht, The Nederlands, 1997.
2. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
3. (c) Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheronii, N. Coord, Chem. Rev. 2000, 205, 59.
4. (d) de Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev. 2000, 205, 41.
5. (a) Benoit, J. M.; Fitzgerald, W. F.; Damman, A. W. Environ. Res. 1998, 78, 118.
6. (b) Renzoni, A.; Zino, F.; Franchi, E. Environ. Res. 1998, 77, 68.
7. (c) Malm, O. Environ. Res. 1998, 77, 73.
8. (d) Mercury Update: Impact on Fish Advisories. EPA Fact Sheet EPA-823-F-01-011; EPA. Office of Water. Washington, DC. 2001. 3.
9. (a) Grandjean, P.; Weihe, P.; White, R. F.; Debes, F. Environ. Res. 1998, 77, 165.
10. (b) Takeuchi, T.; Morikawa, N.; Matsumoto, N. H.; Siraishi, Y. Acta Neuropathol. 1962, 2, 40.
11. (c) Harada, M. Crit. Rev. Toxicol. 1995, 52, 1.
12. (a) Linder, M. C.; Hazegh-Azam, M. Am. J. Clin, Nutr. 1996, 63, 797S.
13. (b) Uauy, R.; Olivares, M.; Gonzalez, M. Am. J. Clin, Nutr. 1998, 67, 952S.
14. (a) Georgopoulos, P. G.; Roy, A.; Yonone-Lioy, M. J.; Opiekun, R. E.; Lioy, P. J. J. Toxicol. Env. Health, B 2001, 4, 341.
15. (b) The U. S. Environmental Protection Agency (EPA) has set the limit of copper in drinking water to be 1.3 ppm. 6. A few selected examples of sensors for Hg2+ and Cu2+:
16. (a) Wu, Q.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 14682.
17. (b) Gunnlaugsson, T.; Leonard, J. P.; Murray, N. S. Org. Lett. 2004, 6, 1557.
18. (c) Coronado, E.; Galán-Mascarós, J. R.; Martí-Gastaldo, C.; Palomares, E.; Durrant, J. R.; Vilar, R.; Grätzel M.; Nazeeruddin, M. K. J. Am. Chem. Soc. 2005, 127, 12351.
19. (d) Ros-Lis, J. V.; Marcos, M. D.; Martínez-Máñez, R.; Rurack, K.; Soto, J. Angew. Chem. Int. Ed. 2005, 44, 4405;
20. (e) Kim, I. B.; Bunz, U. H. F. J. Am. Chem. Soc. 2006, 128, 2818.
21. (f) Zhao, Y.; Zhong, Z. Q. Org. Lett. 2006, 8, 4715.
22. (g) Zhao Y.; Zhong, Z. Q. J. Am. Chem. Soc. 2006, 128, 9988;
23. (h) Balaji, T.; El-Safty, S. A.; Matsunaga, H.; Hanaoka T.; Mizukami, F. Angew. Chem. Int. Ed. 2006, 45, 7202.
24. (i) Lin, S. Y.; Wu S. M.; Chen, C. H. Angew. Chem. Int. Ed. 2006, 45, 4948.
25. (j) Diez-Gil, C.; Caballero, A.; Ratera, I.; Tárraga, A.; Molina P.; Veciana, J. Sensors 2007, 7, 3481.
26. (k) Diez-Gil, C.; Martínez, R.; Ratera, I.; Tárraga, A.; Molina, P.; Veciana J. J. Mater. Chem. 2008, 18, 1997.
27. (l) Yuan, M.; Zhou, W.; Liu, X.; Zhu, Li, J.; Yin, X.; Zheng, H.; Zuo, Z.; Ouyang, C.; Liu, H.; Li, Y.; Zhu, D. J. Org. Chem. 2008, 53, 5008.
28. (m) Wu, D.; Huang, W.; Lin, Z.; Duan, C.; He, C.; Wu, S.; Wang, D. Inorg. Chem. 2008, 47, 7190.
29. (n) Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443.
30. For a review see: Molina, P.; Tárraga, A.; Caballero, A. Eur. J. Inorg. Chem. 2008, 3401.
31. (a) Caballero, A.; Martínez, R.; Lloveras, V.; Ratera, I.; Vidal-Gancedo, J.; Wurst, K.; Tárraga, A.; Molina, P.; Veciana, J. J. Am. Chem. Soc. 2005, 127, 15666.
32. (b) Martínez, R.; Zapata, F.; Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. Org. Lett. 2006, 8, 3235.
33. (c) Caballero, A.; Lloveras, V.; Curiel, D.; Tárraga, A.; Espinosa, A.; García, R.; Vidal-Gancedo, J.; Rovira, C.; Wurst, K.; Molina, P.; Veciana, J. Inorg. Chem. 2007, 46, 825.
34. (d) Caballero, A.; Espinosa, A.; Tarraga, A.; Molina, P. J. Org. Chem. 2008, 73, 5489.
35. (e) Oton, F.; Espinosa, A.; Tarraga, A.; Ratera, I.; Wurst, K.; Veciana, J.; Molina, P. Inorg. Chem. 2009, 48, 1566.
36. (f) Romero, T.; Caballero, A.; Espinosa, A.; Tarraga, A.; Molina, P. Dalton Trans, 2009, DOI 10.1039/b819778d
37. Davidsen, S. K.; Phillips G. W.; Martin, S. F. Org. Synth. 1993, 8, 451.
38. Lloveras, V.; Caballero, A.; Tarraga, A.; Velasco, M. D.; Espinosa, A.; Wurst, K.; Evans, D. J.; Vidal-Gancedo, J.; Rovira, C.; Molina, P.; Veciana, J. Eur. J. Inorg. Chem. 2005, 2436.
39. (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 and references cited therein.
40. (b) Ando, K. J. Org. Chem. 1997, 62, 1934.
41. (c) Ando, K. J. Org. Chem. 1998, 63, 8411-8416.
42. (d) Wang, Y.; West, F. G. Synthesis 2002, 99.
43. All processes observed were reversible, according to the criteria of (i) separation of 60 mV between cathodic and anodic peaks, (ii) close-to-unity ratio of the intensities of the cathodic and anodic currents, and (iii) constancy of the peak potential on changing sweep rate in the CVs. The same halfwave potential values have been obtained from the DPV peaks and from an average of the cathodic and anodic cyclic voltammetric peak. 13.
44. (a) Forster, T.; Kasper, K. Z. Elektrochem. 1955, 59, 976-980.
45. (b) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
46. Barlow, S.; Bunting, H. E.; Ringham, C.; Green, J. C.; Bublitz, G. U.; Boxer, S. G.; Perry, J. W.; Marder, S. R. J. Am. Chem. Soc. 1999, 121, 3715.
47. (a) Winnick, F. M. Chem. Rev. 1993, 93, 587.
48. (b) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463.
49. (c) Sahoo, D.; Narayanaswami, V.; Kay C. M.; Ryan, R. O. Biochemistry 2000, 29, 6594.
50. (d) Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 61, 8551.
51. φ = 0.005 for 7, φ = 0.016 for 9, φ = 0.022 for 10, φ = 0.080 for 11.
52. 2+was used as their trifluoromethanesulfonate salt.
53. Specfit/32 Global Analysis System, 1999-2004, Spectrum Software Associates (SpecSoft@compuserve.com).
54. DPV technique has been employed to obtain well-resolved potential information, while the individual redox process are poorly resolved in the CV experiments in individual E1/2 potential can not be easily accurately extracted from this data. See: Serr, B. R.; Andersen, K. A.; Elliot, C. M.; Anderson, O. P. Inorg. Chem. 1988, 27, 4499.
55. Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414.
56. Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J. Phys. Chem. A 1998, 102, 3782.
57. (a) Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2004, 108, 6908.
58. (b) Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A, 2005, 109, 5656.
59. For instance, see: Muniz, J.; Sansores, L. E.; Martinez, A.; Salcedo, R. J. Mol. Struct. 2007, 820, 141.
60. Bader, R. F. W. Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, 1990.
61. -2 au.
62. Nakanishi, W.; Nakamoto, T.; Hayashi, S.; Sasamori T.; Tokitoh, N. Chem. Eur. J. 2007, 13, 255 and references cited therein.
63. Lupan, S.; Kapon, M.; Cais, M.; Herbstein, F. H. Angew. Chem. 1972, 84, 1104.
64. Angew. Chem. Int. Ed. 1972, 11, 1025
65. a ring.
66. Gaussian 03, Revision B.03, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Inc., Wallingford CT, 2004.
67. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
68. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comp. Chem. 2003, 24, 669.
69. (a) Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117.
70. (b) Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 5631.
71. Wiberg, K. Tetrahedron 1968, 24, 1083.
72. (a) AIM2000 v. 2.0, designed by Biegler-Konig, F. W. and Schonbohm, J. 2002. Home page http://www.aim2000.de/.
73. Biegler-Konig, F.; Schonbohm, J.; Bayles, D. J. Comp. Chem. 2001, 22, 545.
74. (b) Biegler-Konig, F.; Schonbohm, J. J. Comp. Chem. 2002, 23, 1489.