Colorimetric sensing of cyanide anion in aqueous media with a fluorescein-spiropyran conjugate

Tetrahedron

Volumn 68, Issue 2, 2012, Pages 690-696

  Sumiya, Shigehiro ^a   Doi, Takayuki ^a   Shiraishi, Yasuhiro ^a   Hirai, Takayuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Cyanide; Fluorescein; Receptor; Spiropyran; Water

Indexed keywords

ANION; CHROMIC ACID; CYANIDE; FLUORESCEIN; MEROCYANINE; SPIROPYRAN; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; COLORIMETRY; ISOMERIZATION; KINETICS; NUCLEOPHILICITY; PRIORITY JOURNAL; ULTRAVIOLET IRRADIATION;

EID: 82955233693     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.097     Document Type: Article

References (46)

1. R. Koenig Science 287 2000 1737 1738
2. M.A. Holland, and L.M. Kozlowski Clin. Pharm. 5 1986 737 741
3. J.D. Johnson, T.L. Meisenheimer, and G.E. Isom Toxicol. Appl. Pharmacol. 84 1986 464 469
4. B.K. Ardelt, J.L. Borowitz, and G.E. Isom Toxicology 56 1989 147 154
5. U. EPA Fed. Regist. 63 1998 44511 44536
6. K. Ikebukuro, H. Nakamusa, and I. Karube L.M.L. Nollet, Handbook of Water Analysis Vol. 102 2000 Marcel Dekker New York, NY 367 385
7. L.S. Clesceri, A.E. Greenberg, A.D. Eaton, and M.A.H. Franson Standard Methods for the Examination of Water and Wastewater 20th ed. 1998 Water Environment Federation, American Public Health Association Washington, DC
8. C. Young, L. Tidwell, and C. Anderson Cyanide: Social, Industrial and Economic Aspects 2001 Minerals, Metals, and Materials Society Warrendale
9. Ullman's Encyclopedia of Industrial Chemistry 6th ed. 1999 Wiley-VCH New York, NY
10. H. Miyaji, and J.L. Sessler Angew. Chem., Int. Ed. 40 2001 154 157
11. S.-J. Hong, J. Yoo, S.-H. Kim, J.S. Kim, J. Yoon, and C.-H. Lee Chem. Commun. 2009 189 191 Fluorometric receptors
12. P. Anzenbacher Jr., D.S. Tyson, K. Jursíková, and F.N. Castellano J. Am. Chem. Soc. 124 2002 6232 6233
13. K. Parab, K. Venkatasubbaiah, and F. Jäkle J. Am. Chem. Soc. 128 2006 12879 12885
14. X. Lou, L. Zhang, J. Qin, and Z. Li Chem. Commun. 2008 5848 5850
15. P. Fuertes, D. Moreno, J.V. Cuevas, M. García-Valverde, and T. Torroba Chem. - Asian J. 5 2010 1692 1699 Fluorometric receptors
16. M. Jamkratoke, V. Ruangpornvisuti, G. Tumcharern, T. Tuntulani, and B. Tomapatanaget J. Org. Chem. 74 2009 3919 3922
17. S.K. Kwon, S. Kou, H.N. Kim, X. Chen, H. Hwang, S.-W. Nam, S.H. Kim, K.M.K. Swamy, S. Park, and J. Yoon Tetrahedron Lett. 49 2008 4102 4105
18. Y. Shiraishi, K. Adachi, M. Itoh, and T. Hirai Org. Lett. 11 2009 3482 3485
19. Y. Shiraishi, M. Itoh, and T. Hirai Tetrahedron 67 2011 891 897
20. R. Weissleder, and V. Ntziachristos Nat. Med. 9 2003 123 128
21. X. Chen, Z. Li, Y. Xiang, and A. Tong Tetrahedron Lett. 49 2008 4697 4700
22. T. Li, Z. Yang, Y. Li, Z. Liu, G. Qi, and B. Wang Dyes Pigm. 88 2011 103 108
23. L.A. Cabell, M.-K. Monahan, and E.V. Anslyn Tetrahedron Lett. 40 1999 7753 7756
24. W. Liu, L. Xu, R. Sheng, P. Wang, H. Li, and S. Wu Org. Lett. 9 2007 3829 3832
25. W.-C. Sun, K.R. Gee, D.H. Klaubert, and R.P. Haugland J. Org. Chem. 62 1997 6469 6475
26. G. Berkovic, V. Krongauz, and V. Weiss Chem. Rev. 100 2000 1741 1753
27. V.I. Minkin Chem. Rev. 104 2004 2751 2776
28. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman Jr., J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision B.05 2004 Gaussian Wallingford CT
29. J. Hobley, U. Pfeifer-Fukumura, M. Bletz, T. Asahi, H. Masuhara, and H. Fukumura J. Phys. Chem. A 106 2002 2265 2270
30. J.-Y. Hasegawa, S. Bureekaew, and H. Nakatsuji J. Photochem. Photobiol., A 189 2007 205 210
31. W.O. Parker Jr., J. Hobley, and V. Malatesta J. Phys. Chem. A 106 2002 4028 4031
32. K. Machitani, M. Nakamura, H. Sakamoto, N. Ohata, H. Masuda, and K. Kimura J. Photochem. Photobiol. A: Chem. 200 2008 96 100
33. S. Yagi, S. Nakamura, D. Watanabe, and H. Nakazumi Dyes Pigm. 80 2009 98 105
34. X. Guo, Y. Zhou, D. Zhang, B. Yin, Z. Liu, C. Liu, Z. Lu, Y. Huang, and D. Zhu J. Org. Chem. 69 2004 8924 8931
35. R. Sjöback, J. Nygren, and M. Kubista Spectrochim. Acta, A 51 1995 L7 21
36. G.R. Fleming, A.W.E. Knight, J.M. Morris, R.J.S. Morrison, and G.W. Robinson J. Am. Chem. Soc. 99 1977 4306 4311
37. G.A. Hebbink, L. Grave, L.A. Woldering, D.N. Reinhoudt, and F.C.J.M. van Veggel J. Phys. Chem. A 107 2003 2483 2491
38. C.A. Heller, D.A. Fine, and R.A. Henry J. Phys. Chem. 65 1961 1908 1909
39. Y. Shiraishi, M. Itoh, and T. Hirai Tetrahedron Lett. 52 2011 1515 1519
40. H.D. Banks J. Org. Chem. 68 2003 2639 2644
41. M.L. Kuznetsov J. Mol. Struct. 674 2004 33 42
42. C.A. Parker, and W.T. Rees Analyst 85 1960 587 600
43. Y. Shiraishi, S. Sumiya, and T. Hirai Chem. Commun. 47 2011 4953 4955
44. Y. Shiraishi, N. Saito, and T. Hirai J. Am. Chem. Soc. 127 2005 8304 8306
45. R.E. Stratmann, G.E. Scuseria, and M.J. Frisch J. Chem. Phys. 109 1998 8218 8224
46. M. Cossi, V. Barone, R. Cammi, and J. Tomasi Chem. Phys. Lett. 255 1996 327 335