Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Fluorescence Sensing Properties of Thiazolobenzo-crown Ether Incorporating Coumarin

  • Lee, Sang-Hoon (Department of Applied Chemistry, Kyungpook National University) ;
  • Helal, Aasif (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
  • Published : 2010.03.20
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Abstract

A new coumarin-thiazolobenzo-crown ether based fluorogenic chemosensor BTC (1) was reported. The ion-selective binding properties of 1 with different alkali, alkaline earth metals and transitional metals were investigated in an ethanol-DMSO system. BTC (1) showed the highest binding constant toward $Hg^{2+}$ over $Ag^+$, $Pb^{2+}$ and $Cu^{2+}$.

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References

  1. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495. https://doi.org/10.1021/ja00986a052
  2. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3. https://doi.org/10.1016/S0010-8545(00)00246-0
  3. Berson,J.; Pouget, J.; Valuer, B. J. Phys. Chem. 1993, 97, 4552. https://doi.org/10.1021/j100119a050
  4. deSilva, 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. https://doi.org/10.1021/cr960386p
  5. Sause, L. H.; Larson, J. M. J. Am. Chem. Soc. 1977,99, 307. https://doi.org/10.1021/ja00443a084
  6. Alonso, M. T.; Brunet, E.; Hernandez, C.; Rodrigez-Ubis, J. C. Tetrahedron Lett. 1993, 34, 7465. https://doi.org/10.1016/S0040-4039(00)60154-5
  7. Kim, H.-S.; Koh, Y. K.; Choi, J. H. J. Heterocycl. Chem. 1998,35, 177. https://doi.org/10.1002/jhet.5570350134
  8. Kim, H.-S.; Park, H. J.; Oh, H. J.; Koh, Y. K.; Choi, J.H.; Lee, D. H.; Cha, G. S.; Nam, H. Anal. Chem. 2000, 72, 4683. https://doi.org/10.1021/ac000177b
  9. Kariuki, B. M.; Lee, S.-O.; Harris, K. D. M.; Kim, H.-S.; Do, K.-S.;Kim, K.-I. Cryst. Growth & Des. 2002, 2, 309. https://doi.org/10.1021/cg020008f
  10. Kim, H.-S.; Do,K. S.; Kim, K. S.; Shim, J. H.; Cha, G. S.; Nam, H. Bull. KoreanChem. Soc. 2004, 25, 1465. https://doi.org/10.5012/bkcs.2004.25.10.1465
  11. Kim, H.-S.; Bae, S. Y.; Kim, K. S.;Choi, J. H.; Choi, H. J.; Shim, J. H.; Cha, G. S.; Nam, H. Bull.Korean Chem. Soc. 2008, 29, 417. https://doi.org/10.5012/bkcs.2008.29.2.417
  12. Kwon, O. S.; Kim, H.-S. Supramolecular Chem. 2007, 19, 277. https://doi.org/10.1080/10610270701416497
  13. Leray, I.; Habib-Jiwan, J.-L.; Branger, C.; Soumillion, J.-Ph.;Valeur, B. J. Photochem. Photobiol. 2000, 135, 163. https://doi.org/10.1016/S1010-6030(00)00285-9
  14. Fery-Forgues,S.; Le Bris, M. T.; Guette, J. P.; Valeur, B. J. Phys. Chem. A1988, 92, 6233. https://doi.org/10.1021/j100333a013
  15. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Chem. Rev.2004, 104, 3059. https://doi.org/10.1021/cr030037c
  16. Katerinopoulos, H. E. Current Pharmaceutical Design 2004, 10,3835. https://doi.org/10.2174/1381612043382666
  17. Habib Jiwan, J.-L.; Branger, C.; Soumillion, J.-Ph.; Valeur. B.J. Photochem. Photobiol. 1998, 116, 127. https://doi.org/10.1016/S1010-6030(98)00286-X
  18. Brunet, E.; Garcia-Losada, P.; Rodriguez-Ubis, J.-C.; Juanes, O. Can. J. Chem. 2002,80, 169. https://doi.org/10.1139/v02-006
  19. Badaoui, F. Z.; Bourson, J. Anal. Chim. Acta 1995, 302, 341. https://doi.org/10.1016/0003-2670(94)00495-8
  20. Bourson, J.; Borrel, M.-N.; Valeur, B. Anal. Chim. Acta 1992, 257,189. https://doi.org/10.1016/0003-2670(92)85170-B
  21. Vaidya, B.; Zak, J.; Bastiaans, G. J.; Porter, M. D. Anal. Chem.1995, 67, 4101. https://doi.org/10.1021/ac00118a012
  22. Alonso, M. T.; Brunet, E.; Hernandez, C.; Rodriguez-Ubis, J. C. Tetrahedron Lett. 1993, 34, 7465. https://doi.org/10.1016/S0040-4039(00)60154-5
  23. Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443. https://doi.org/10.1021/cr068000q
  24. Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302. https://doi.org/10.1021/ar00046a003
  25. de Silva, A.P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev.2000, 205, 41. https://doi.org/10.1016/S0010-8545(00)00238-1
  26. Chen, X.; Nam, S. W.; Jou, M. J.; Kim, Y. M.;Kim, S. J.; Park, S. S.; Yoon, J. Y. Organic Lett. 2008, 10, 5235. https://doi.org/10.1021/ol8022598
  27. Wei, J.; Wei, W. Chem. Comm. 2009, 3913.
  28. Mello, J. V.;Finney, N. S. J. Am. Chem. Soc. 2005, 127, 10124. https://doi.org/10.1021/ja043682p
  29. Tatay, S.;Gavina, P.; Coronado, E.; Palomares, E. Org. Lett. 2006, 8, 3857. https://doi.org/10.1021/ol0615580
  30. Yoon, S.; Miller, E. W.; He, Q.; Do, P. H.; Chang, C. J. Angew.Chem. Int. Ed. 2007, 46, 6658. https://doi.org/10.1002/anie.200701785
  31. Davidson, P. W.; Myers, G. J.; Cox, C.; Shamlaye, C. F.; Marsh, D.O.; Tanner, M. A.; Berlin, M.; Sloane-Reeves, J.; Cernichiari, E.;Choisy, O.; Choi, A.; Clarkson, T. W. Neurotoxicology 1995, 16,677.
  32. Takeuchi, T.; Morikawa, N.; Matsumoto, H.; Shiraishi, Y. ActaNeuropathol. 1962, 2, 40. https://doi.org/10.1007/BF00685743
  33. Harada, M. Crit. Rev. Toxicol. 1995, 25, 1. https://doi.org/10.3109/10408449509089885
  34. Lee, M. H.; Cho, B.-K.; Yoon, J.; Kim, J. S. Org. Lett. 2007, 9,4515. https://doi.org/10.1021/ol7020115
  35. Cheng, Y.; Zhang, M.; Yang, H.; Li, F.; Yi, T.; Huang, C.Dye&Pig. 2008, 76, 775.
  36. Cheng, Y.; Zhao, D.; Zhang, M.; Liu, Z.; Zhou, Y.; Shu, T.; Li, F.;Yi, T.; Huang, C. Tetrahedron Lett. 2006, 47, 6413. https://doi.org/10.1016/j.tetlet.2006.06.125
  37. Talanov, V. S.; Roper, E. D.; Buie, N. M.; Talanova, G. G. TetrahedronLett. 2007, 48, 8022. https://doi.org/10.1016/j.tetlet.2007.09.043
  38. Choi, M. G.; Kim, Y. H.; Namgoong, J. E.; Chang, S.-K. Chem.Commun. 2009, 3560.
  39. Leray, I.; Valeur, B. Eur. J. Inorg. Chem. 2009, 3525.
  40. Wang, H.; Chan, W. Tetrahedron 2007, 63, 8825. https://doi.org/10.1016/j.tet.2007.06.026
  41. Santra, M.; Ryu, D.; Chatterjee, A.; Ko, S.-K.; Shin, I.; Ahn,K. H. Chem. Commun. 2009, 2115.
  42. Jana, A.; Kim, J. S.; Jung,H. S.; Bharadwaj, P. K. Chem. Commun. 2009, 4417.
  43. Yang, H.; Zhou, Z.; Xu, J.; Li, F.; Yi, T.; Huang, C. Tetrahedron2007, 63, 6732. https://doi.org/10.1016/j.tet.2007.04.086
  44. Lee, M. H.; Lee, S. W.; Kim, S. H.; Kang, C.; Kim, J. S. Org.Lett. 2009, 11, 2101. https://doi.org/10.1021/ol900542y
  45. Dolci, L. S.; Marzocchi, E.; Montalti, M.;Prodi, L.; Monti, D.; Di Natale, C.; D’Amico, A.; Paolesse, R. Biosens.Bioelectron. 2006, 22, 399. https://doi.org/10.1016/j.bios.2006.05.013
  46. Choi, M. G.; Ryu, D. H.; Jeon, H. L.; Cha, S.; Cho, J.; Joo, H. H.;Hong, K. S.; Lee, C.; Ahn, S.; Chang, S.-K. Org. Lett. 2008, 10,3717. https://doi.org/10.1021/ol8013446
  47. Nolan, E. M.; Racine, M. E.; Lippard, S. J. Inorg. Chem.2006, 45, 2742. https://doi.org/10.1021/ic052083w
  48. Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc.2003, 125, 14270. https://doi.org/10.1021/ja037995g
  49. Nolan, E. M.; Lippard, S. J. J. Am. Chem.Soc. 2007, 129, 5910. https://doi.org/10.1021/ja068879r
  50. Erk, C.; Fresenius, Z. Anal. Chem. 1983, 316, 477. https://doi.org/10.1007/BF00555982
  51. Erk, C. J.Phys. Chem. 1990, 94, 8617. https://doi.org/10.1021/j100386a025
  52. Sousa, L. R.; Larson, M. J. Am. Chem. Soc. 1983, 100, 477.
  53. Valeur, B. Molecular Luminescence Spectroscopy; Schulman, S.G., Ed., John Wiley: New York, 1993; Part 3, pp 25-84.
  54. Schneider, H. J.; Dur, H. Frontiers in Supramolecular Chemistryand Photochemistry; VCH: Weinheim, 1991.
  55. Tran, A. H.; Miller, D. O.; Georghiou, P. E. J. Org. Chem. 2005, 70,1115. https://doi.org/10.1021/jo0484427
  56. Desvergne, J. P.; Czarnik, A. W. NATO ASI Series; KluwerAcademic Publishers: Dordrecht, 1997; Series C, Vol. 492.
  57. deSilva, A. P.; Gunaratne, H. Q. N.; Gunnalaugsson, T.; Manabe, O.J. Chem. Soc. Chem. Commun. 1996, 967.
  58. Connors, K. A. Binding Constants: the Measurement of MolecularComplex Stability; Wiley: New York, 1987; pp 21-101; 339-343.
  59. gnuplot, www.gnuplot.com.
  60. Miyaji, H.; Kim, H.-K.; Sim, E.-K.; Lee, C.-K.; Cho, W.-S.; Sessler,J. L.; Lee, C.-H. J. Am. Chem. Soc. 2005, 127, 12510. https://doi.org/10.1021/ja053612y

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