Reactivity-based detection of copper(II) ion in water: Oxidative cyclization of azoaromatics as fluorescence turn-on signaling mechanism

Journal of the American Chemical Society

Volumn 134, Issue 38, 2012, Pages 16000-16007

  Jo, Junyong ^a   Lee, Ho Yong ^a   Liu, Wenjun ^a   Olasz, András ^a   Chen, Chun Hsing ^a   Lee, Dongwhan ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; BENZOTRIAZOLES; CATHODIC SHIFTS; COPPER IONS; CYCLIZATION REACTIONS; ELECTROCHEMICAL STUDIES; ELECTRON TRANSFER; ELECTRON-DONATING; FIVE-MEMBERED RINGS; GREEN EMISSIONS; HYDROGEN BONDING NETWORK; ONSET POTENTIAL; OXIDATION POTENTIALS; OXIDATIVE CYCLIZATION; ROOM TEMPERATURE; SIGNALING MECHANISMS; STRUCTURAL ANALOGUE; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

CYCLIZATION; FLUORESCENCE; HYDROGEN BONDS; IONS; REACTION RATES; X RAY CRYSTALLOGRAPHY;

COPPER;

2 (PHENYLAZO)ANILINE; ANILINE DERIVATIVE; CUPRIC ION; UNCLASSIFIED DRUG; WATER;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; ELECTRON; ELECTRON TRANSPORT; FLUORESCENCE; HYDROGEN BOND; OXIDATION; OXIDATION REDUCTION POTENTIAL; PROTON TRANSPORT; ROOM TEMPERATURE; X RAY CRYSTALLOGRAPHY;

AZO COMPOUNDS; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FLUORESCENCE; OXIDATION-REDUCTION; WATER;

EID: 84866708783     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307316s     Document Type: Article

References (92)

1. Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308
2. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202
3. Chemosensors of Ion and Molecule Recognition; Desvergne, J. P.; Czarnik, A. W., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997.
4. 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
5. Amendola, V.; Fabbrizzi, L.; Licchelli, M.; Mangano, C.; Pallavicini, P.; Parodi, L.; Poggi, A. Coord. Chem. Rev. 1999, 190-192, 649-669
6. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574
7. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3-40
8. de Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev. 2000, 205, 41-57
9. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59-83
10. Rurack, K.; Resch-Genger, U. Chem. Soc. Rev. 2002, 31, 116-127
11. de Silva, A. P.; McCaughan, B.; McKinney, B. O. F.; Querol, M. Dalton Trans. 2003, 1902-1913
12. Martínez-Mánez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419-4476
13. Advanced Concepts in Fluorescence Sensing. Part A: Small Molecule Sensing; Geddes, C. D.; Lakowicz, J. R., Eds.; Springer: New York, 2005; Vol. 9.
14. Thomas, S. W., III; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339-1386
15. Anslyn, E. V. J. Org. Chem. 2007, 72, 687-699
16. Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443-3480
17. Domaille, D. W.; Que, E. L.; Chang, C. J. Nat. Chem. Biol. 2008, 4, 168-175
18. Nolan, E. M.; Lippard, S. J. Acc. Chem. Res. 2009, 42, 193-203
19. Xu, Z.; Yoon, J.; Spring, D. R. Chem. Soc. Rev. 2010, 39, 1996-2006
20. Lee, D. In Chemosensors: Principles, Strategies, and Applications; Wang, B.; Anslyn, E. V., Eds.; John Wiley & Sons: Hoboken, NJ, 2011, p 41-64.
21. Que, E. L.; Domaille, D. W.; Chang, C. J. Chem. Rev. 2008, 108, 1517-1549
22. Kim, B.-E.; Nevitt, T.; Thiele, D. J. Nat. Chem. Biol. 2008, 4, 176-185
23. Boal, A. K.; Rosenzweig, A. C. Chem. Rev. 2009, 109, 4760-4779
24. Bush, A. I. Curr. Opin. Chem. Biol. 2000, 4, 184-191
25. Millhauser, G. L. Acc. Chem. Res. 2004, 37, 79-85
26. Donnelly, P. S.; Xiao, Z.; Wedd, A. G. Curr. Opin. Chem. Biol. 2007, 11, 128-133
27. Madsen, E.; Gitlin, J. D. Annu. Rev. Neurosci. 2007, 30, 317-337
28. Gaggelli, E.; Kozlowski, H.; Valensin, D.; Valensin, G. Chem. Rev. 2006, 106, 1995-2044
29. Gh Popescu, B. F.; Nichol, H. CNS Neurosci. Ther. 2011, 17, 256-268
30. Bergonzi, R.; Fabbrizzi, L.; Licchelli, M.; Mangano, C. Coord. Chem. Rev. 1998, 170, 31-46
31. Royzen, M.; Dai, Z.; Canary, J. W. J. Am. Chem. Soc. 2005, 127, 1612-1613
32. Xu, Z.; Qian, X.; Cui, J. Org. Lett. 2005, 7, 3029-3032
33. Xu, Z.; Xiao, Y.; Qian, X.; Cui, J.; Cui, D. Org. Lett. 2005, 7, 889-892
34. Wen, Z.-C.; Yang, R.; He, H.; Jiang, Y.-B. Chem. Commun. 2006, 106-108
35. Goswami, S.; Sen, D.; Das, N. K. Org. Lett. 2010, 12, 856-859
36. Xu, Z.; Pan, J.; Spring, D. R.; Cui, J.; Yoon, J. Tetrahedron 2010, 66, 1678-1683
37. For a phosphorescence-based copper(II) imaging agent, see: You, Y.; Han, Y.; Lee, Y.-M.; Park, S. Y.; Nam, W.; Lippard, S. J. J. Am. Chem. Soc. 2011, 133, 11488-11491
38. Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2012, 112, ASAP.
39. Kaur, K.; Saini, R.; Kumar, A.; Luxami, V.; Kaur, N.; Singh, P.; Kumar, S. Coord. Chem. Rev. 2012, 256, 1992-2028
40. Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2011, 112, 1910-1956
41. Quang, D. T.; Kim, J. S. Chem. Rev. 2010, 110, 6280-6301
42. Cho, D.-G.; Sessler, J. L. Chem. Soc. Rev. 2009, 38, 1647-1662
43. Dujols, V.; Ford, F.; Czarnik, A. W. J. Am. Chem. Soc. 1997, 119, 7386-7387
44. Kovács, J.; Rödler, T.; Mokhir, A. Angew. Chem. Intl. Ed. 2006, 45, 7815-7817
45. Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Org. Lett. 2006, 8, 2863-2866
46. Qi, X.; Jun, E. J.; Xu, L.; Kim, S.-J.; Hong, J. S. J.; Yoon, Y. J.; Yoon, J. J. Org. Chem. 2006, 71, 2881-2884
47. Zhang, X.; Shiraishi, Y.; Hirai, T. Org. Lett. 2007, 9, 5039-5042
48. Swamy, K. M. K.; Ko, S.-K.; Kwon, S. K.; Lee, H. N.; Mao, C.; Kim, J.-M.; Lee, K.-H.; Kim, J.; Shin, I.; Yoon, J. Chem. Commun. 2008, 5915-5917
49. Kim, M. H.; Jang, H. H.; Yi, S.; Chang, S.-K.; Han, M. S. Chem. Commun. 2009, 4838-4840
50. Zhao, Y.; Zhang, X.-B.; Han, Z.-X.; Qiao, L.; Li, C.-Y.; Jian, L.-X.; Shen, G.-L.; Yu, R.-Q. Anal. Chem. 2009, 81, 7022-7030
51. Zhou, Y.; Wang, F.; Kim, Y.; Kim, S.-J.; Yoon, J. Org. Lett. 2009, 11, 4442-4445
52. Yu, F.; Zhang, W.; Li, P.; Xing, Y.; Tong, L.; Ma, J.; Tang, B. Analyst 2009, 134, 1826-1833
53. Wang, Q.-L.; Zhang, H.; Jiang, Y.-B. Tetrahedron Lett. 2009, 50, 29-31
54. Li, N.; Xiang, Y.; Tong, A. Chem. Commun. 2010, 46, 3363-3365
55. Zhang, J. F.; Zhou, Y.; Yoon, J.; Kim, Y.; Kim, S. J.; Kim, J. S. Org. Lett. 2010, 12, 3852-3855
56. Kumar, M.; Kumar, N.; Bhalla, V.; Sharma, P. R.; Kaur, T. Org. Lett. 2012, 14, 406-409
57. Zhao, C.; Feng, P.; Cao, J.; Wang, X.; Yang, Y.; Zhang, Y.; Zhang, J.; Zhang, Y. Org. Biomol. Chem. 2012, 10, 3104-3109
58. Liu, W.-Y.; Li, H.-Y.; Zhao, B.-X.; Miao, J.-Y. Analyst 2012, 137, 3466-3469
59. Liu, J.; Lu, Y. J. Am. Chem. Soc. 2007, 129, 9838-9839
60. Liu, M.; Zhao, H.; Chen, S.; Yu, H.; Zhang, Y.; Quan, X. Chem. Commun. 2011, 47, 7749-7751
61. Schmidt, M. P.; Hagenböcker, A. Chem. Ber. 1921, 54, 2191-2200
62. Schmidt, M. P.; Hagenböcker, A. Chem. Ber. 1921, 54, 2201-2207
63. Nigh, W. G. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: London, 1973; Vol. 5B, pp 1-96.
64. Carboni, R. A.; Kauer, J. C.; Castle, J. E.; Simmons, H. E. J. Am. Chem. Soc. 1967, 89, 2618-2625
65. Hall, J. H. J. Org. Chem. 1968, 33, 2954-2956
66. Carboni, R. A.; Castle, J. E. J. Am. Chem. Soc. 1962, 84, 2453-2454
67. Carboni, R. A.; Kauer, J. C.; Hatchard, W. R.; Harder, R. J. J. Am. Chem. Soc. 1967, 89, 2626-2633
68. Kauer, J. C.; Carboni, R. A. J. Am. Chem. Soc. 1967, 89, 2633-2637
69. Zincke, T.; Th Lawson, A. Chem. Ber. 1887, 20, 1176-1183
70. Zincke, T.; Jaenke, H. Chem. Ber. 1888, 21, 540-548
71. Dyall, L. K. Aust. J. Chem. 1979, 32, 643-651
72. Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1975, 97, 6151-6154
73. Butler, R. N. Chem. Rev. 1984, 84, 249-276
74. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
75. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; 3 rd ed.; Springer: New York, 2006.
76. Valeur, B. Molecular Fluorescence: Principles and Applications; Wiley-VCH: Weinheim, Germany, 2002.
77. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358
78. Reichardt, C.; Welton, T. Solvents and Solvent Effects in Organic Chemistry; 4 th ed.; Wiley-VCH: Weinheim, 2010.
79. Burlov, A. S.; Uraev, A. I.; Lysenko, K. A.; Chigarenko, G. G.; Ponomarenko, A. G.; Matuev, P. V.; Nikolaevskii, S. A.; Garnovskaya, E. D.; Borodkin, G. S.; Garnovskii, A. D. Russ. J. Coord. Chem. 2006, 32, 686-691
80. Burlov, A. S.; Uraev, A. I.; Matuev, P. V.; Lysenko, K. A.; Kamkin, N. N.; Garnovskii, D. A.; Nikolaevskii, S. A.; Kogan, V. A.; Garnovskii, A. D. Russ. J. Coord. Chem. 2008, 34, 904-910
81. Price, R.; Yates, J. E. J. Chem. Soc., Perkin Trans. 1 1982, 1775-1782
82. Liss, T. A.; Baer, D. R. Inorg. Chem. 1969, 8, 1328-1336
83. Maciejewska, D.; Wolska, I.; Kowalska, V. J. Mol. Str. 2004, 693, 27-34
84. Kelemen, J.; Kormány, G.; Rihs, G. Dyes Pigm. 1982, 3, 249-271
85. Zhang, L.; Xia, J.; Li, Q.; Li, X.; Wang, S. Organometallics 2011, 30, 375-378
86. Bohle, D. S.; Dorans, K. S.; Fotie, J. Acta Crystallogr. 2007, E63, o889-o890
87. The Chemistry of the hydrazo, azo and azoxy groups; Patai, S., Ed.; John Wiley & Sons: London, 1975.
88. Sawicki, E. J. Org. Chem. 1957, 22, 915-919
89. Edition of the Drinking Water Standards and Health Advisories (EPA 822-S-12-001); U.S. EPA Office of Science and Technology: Washington, D.C., 2012.
90. Ferlin, M. G.; Via, L. D.; Gia, O. M. Bioorg. Med. Chem. 2004, 12, 771-777
91. Bléger, D.; Ciesielski, A.; Samorí, P.; Hecht, S. Chem.-Eur. J. 2010, 16, 14256-14260
92. Williams, A. T. R.; Winfield, S. A.; Miller, J. N. Analyst 1983, 108, 1067-1071