A boradiazaindacene-based turn-on fluorescent probe for cyanide detection in aqueous media

Chemistry - A European Journal

Volumn 18, Issue 15, 2012, Pages 4513-4516

  Lee, Chi Hwa ^a   Yoon, Hee Jae ^a   Shim, Jeong Soo ^a   Jang, Woo Dong ^a  

^a Yonsei University   (South Korea)

Author keywords

anions; BODIPY; cyanides; fluorescence; sensors

Indexed keywords

AQUEOUS MEDIA; BODIPY; CYANIDE DETECTION; FLUORESCENCE ENHANCEMENT; FLUORESCENT PROBES; MOLECULAR PROBES; SENSITIVE DETECTION;

FLUORESCENCE; NEGATIVE IONS; SENSORS;

CYANIDES;

2,2' BIPYRIDINE; ANION; BORADIAZAINDACENE; BORANE DERIVATIVE; CYANIDE; DRUG DERIVATIVE; FLUORESCENT DYE; VINYL DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; MOLECULAR PROBE;

2,2'-DIPYRIDYL; ANIONS; BORANES; CYANIDES; FLUORESCENT DYES; MOLECULAR PROBES; VINYL COMPOUNDS; WATER;

EID: 84859238631     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200008     Document Type: Article

References (63)

1. C. Miller, Nature 2006, 440, 484
2. R. Dutzler, E. B. Campbell, R. Mackinnon, Science 2003, 300, 108
3. R. Dutzler, E. B. Campbell, M. Cadene, B. T. Chait, R. Mackinnon, Nature 2002, 415, 287
4. R. R. Copley, G. J. Barton, J. Mol. Biol. 1994, 242, 321
5. J. J. He, F. A. Quiocho, Science 1991, 251, 1479
6. H. Luecke, F. A. Quiocho, Nature 1990, 347, 402
7. J. W. Pflugrath, F. A. Quiocho, Nature 1985, 314, 257.
8. K. W. Kulig, Cyanide Toxicity, U. S. Department of Health and Human Services, Atlanta, GA, 1991
9. S. I. Baskin, T. G. Brewer, in Medical Aspects of Chemical and Biological Warfare (Eds.:, F. Sidell, E. T. Takafuji, D. R. Franz,), TMM, Washington, DC, 1997, pp. 271-286.
10. R. Koenig, Science 2000, 287, 1737
11. G. C. Miller, C. A. Pritsos, Cyanide: Soc., Ind., Econ. Aspects, Proc. Symp. Annu. Meet. 2001, 73
12. C. Young, L. Tidwell, C. Anderson, Cyanide: Social, Industrial and Economic Aspects: Minerals, Metals, and Materials Society, Warrendale, 2001.
13. H. J. Kim, K. C. Ko, J. H. Lee, J. Y. Lee, J. S. Kim, Chem. Commun. 2011, 47, 2886
14. S. Saha, A. Ghosh, P. Mahato, S. Mishra, S. K. Mishra, E. Suresh, S. Das, A. Das, Org. Lett. 2010, 12, 3406
15. J. Jo, D. Lee, J. Am. Chem. Soc. 2009, 131, 16283
16. S.-Y. Chung, S.-W. Nam, J. Lim, S. Park, J. Yoon, Chem. Commun. 2009, 2866
17. T. Agou, M. Sekine, J. Kobayashi, T. Kawashima, Chem. Eur. J. 2009, 15, 5056
18. D.-G. Cho, J. H. Kim, J. L. Sessler, J. Am. Chem. Soc. 2008, 130, 12163
19. H. Miyaji, D.-S. Kim, B.-Y. Chang, E. Park, S.-M. Park, K. H. Ahn, Chem. Commun. 2008, 753
20. V. Ganesh, M. P. C. Sanz, J. C. Mareque-Rivas, Chem. Commun. 2007, 5010
21. Y.-K. Yang, J. Tae, Org. Lett. 2006, 8, 5721
22. C.-L. Chen, Y.-H. Chen, C.-Y. Chen, S.-S. Sun, Org. Lett. 2006, 8, 5053
23. Y. M. Chung, B. Raman, D.-S. Kim, K. H. Ahn, Chem. Commun. 2006, 186
24. R. Badugu, J. R. Lakowicz, C. D. Geddes, J. Am. Chem. Soc. 2005, 127, 3635
25. Y.-H. Kim, J.-I. Hong, Chem. Commun. 2002, 512.
26. T. T. Christison, J. S. Rohrer, J. Chromatogr. A 2007, 1155, 31
27. A. Safavi, N. Maleki, H. R. Shahbaazi, Anal. Chim. Acta 2004, 503, 213
28. D. Shan, C. Mousty, S. Cosnier, Anal. Chem. 2004, 76, 178
29. T. Suzuki, A. Hiolki, M. Kurahashi, Anal. Chim. Acta 2003, 476, 159
30. V. K. Rao, S. R. Suresh, N. B. S. N. Rao, P. Rajaram, Bull. Electrochem. 1997, 13, 327
31. S. Kage, T. Nagata, K. Kudo, J. Chromatogr. B 1996, 675, 27
32. R. D. Rocklin, E. L. Johnson, Anal. Chem. 1983, 55, 4.
33. P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502
34. Angew. Chem. Int. Ed. 2001, 40, 486
35. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum, New York, 1999
36. P. D. Beer, Acc. Chem. Res. 1998, 31, 71
37. J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995.
38. T. Tachikawa, N. Wang, S. Yamashita, S.-C. Cui, T. Majima, Angew. Chem. 2010, 122, 8775
39. Angew. Chem. Int. Ed. 2010, 49, 8593
40. O. A. Bozdemir, R. Guliyev, O. Buyukcakir, S. Selcuk, S. Kolemen, G. Gulseren, T. Nalbantoglu, H. Boyaci, E. U. Akkaya, J. Am. Chem. Soc. 2010, 132, 8029
41. J. Rosenthal, S. J. Lippard, J. Am. Chem. Soc. 2010, 132, 5536
42. D. W. Domaille, L. Zeng, C. J. Chang, J. Am. Chem. Soc. 2010, 132, 1194
43. O. A. Bozdemir, F. Sozmen, O. Buyukcakir, R. Guliyev, Y. Cakmak, E. U. Akkaya, Org. Lett. 2010, 12, 1400
44. S. C. Dodani, Q. He, C. J. Chang, J. Am. Chem. Soc. 2009, 131, 18020
45. R. Guliyev, A. Coskun, E. U. Akkaya, J. Am. Chem. Soc. 2009, 131, 9007
46. S. Ozlem, E. U. Akkaya, J. Am. Chem. Soc. 2009, 131, 48
47. T. Cheng, Y. Xu, S. Zhang, W. Zhu, X. Qian, L. Duan, J. Am. Chem. Soc. 2008, 130, 16160
48. T. Ueno, Y. Urano, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2006, 128, 10640.
49. M. Takahashi, A. Kawamura, N. Kato, T. Nishi, I. Hamachi, J. Ohkanda, Angew. Chem. 2012, 124, 524
50. Angew. Chem. Int. Ed. 2012, 51, 509
51. D. Ye, G. Liang, M. L. Ma, J. Rao, Angew. Chem. 2011, 123, 3294
52. Angew. Chem. Int. Ed. 2011, 50, 3236.
53. R. Guliyev, S. Ozturk, Z. Kostereli, E. U. Akkaya, Angew. Chem. 2011, 123, 10000
54. Angew. Chem. Int. Ed. 2011, 50, 9826
55. O. Altan Bozdemir, S. Erbas-Cakmak, O. O. Ekiz, A. Dana, E. U. Akkaya, Angew. Chem. 2011, 123, 11099
56. Angew. Chem. Int. Ed. 2011, 50, 10907
57. T. Bura, P. Retailleau, R. Ziessel, Angew. Chem. 2010, 122, 6809
58. Angew. Chem. Int. Ed. 2010, 49, 6659
59. J.-Y. Liu, E. A. Ermilov, B. Röder, D. K. P. Ng, Chem. Commun. 2009, 1517
60. F. Camerel, L. Bonardi, M. Schmutz, R. Ziessel, J. Am. Chem. Soc. 2006, 128, 4548.
61. Y. Cakmak, S. Kolemen, S. Duman, Y. Dede, Y. Dolen, B. Kilic, Z. Kostereli, L. Tatar Yildirim, A. L. Dogan, D. Guc, E. U. Akkaya, Angew. Chem. 2011, 123, 12143
62. S. G. Awuah, J. Polreis, V. Biradar, Y. You, Org. Lett. 2011, 13, 3884.
63. Z. Ekmekci, M. D. Yilmaz, E. U. Akkaya, Org. Lett. 2008, 10, 461.