Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Investigation of Isomerism in Anthracene-Isothiouronium Salts and Application of these Salts for Anion Sensing

  • Nguyen, Quynh Pham Bao (Department of Applied Chemistry and Center for Functional Nano Fine Chemicals, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Taek-Hyeon (Department of Applied Chemistry and Center for Functional Nano Fine Chemicals, Chonnam National University)
  • Published : 2009.09.20
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Abstract

Novel fluorescent anion chemosensors based on anthracene-isothiouronium derivatives were synthesized. Isomerism due to the intramolecular mobility in these isothiouronium salts was detected by $^1H$ NMR spectroscopy. The effect of the substituent, temperature and solvent on the isomerism was also examined. The anthracene-isothiouronium sensor showed significant fluorescent enhancement upon the addition of various anions such as fluoride, acetate, and dihydrogen phosphate, even in the presence of water.

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References

  1. Manez, R. M.; Sancenon, F. Chem. Rev. 2003, 103, 4419-4476 https://doi.org/10.1021/cr010421e
  2. Manez, R. M.; Sancenon, F. Journal of Fluorescene 2005, 15, 267-285 https://doi.org/10.1007/s10895-005-2626-z
  3. Gunnlaugsson, T.; Davis, A. P.; Hussey, G. M.; Tierney, J.; Glynn, M. Org. Biomol. Chem. 2004, 2, 1856-1863 https://doi.org/10.1039/b404706k
  4. Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Biomol. Chem. 2005, 3, 48-56 https://doi.org/10.1039/b409018g
  5. Kim, S. K.; Singh, N. J.; Kim, S. J.; Swamy, K. M. K.; Kim, S. H.; Lee, K. H.; Kim, K. S.; Yoon, J. Tetrahedron 2005, 61, 4545-4550 https://doi.org/10.1016/j.tet.2005.03.009
  6. Kim, Y. K.; Lee, H. N.; Singh, N. J.; Choi, H. J.; Xue, J. Y.; Kim, K. S.; Yoon, J.; Hyun, M. H. J. Org. Chem. 2008, 73, 301-304 https://doi.org/10.1021/jo7022813
  7. Jun, E. J.; Swamy, K. M. K.; Bang, H.; Kim, S. J.; Yoon, J. Tetrahedron Letters 2006, 47, 3103-3106 https://doi.org/10.1016/j.tetlet.2006.02.147
  8. Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc. Perkin Trans. 2 1998, 2325-2327
  9. Chakraborty, S.; Tarr, M. A. Can. J. Chem. 2007, 85, 153-156 https://doi.org/10.1139/V07-009
  10. Liu, S. Y.; Fang, L.; He, Y. B.; Chan, W. H.; Yeung, K. T.; Cheng, Y. K.; Yang, R. H. Org. Lett. 2005, 7, 5825-5828 https://doi.org/10.1021/ol052341t
  11. Yen, Y. P.; Ho, K. W. Tetrahedron Letters 2006, 47, 1193-1196 https://doi.org/10.1016/j.tetlet.2005.12.009
  12. Zeng, Z. Y.; He, Y. B.; Wu, J. L.; Wei, L. H.; Liu, X.; Meng, L. Z.; Yang, X. Eur. J. Org. Chem. 2004, 2888-2893
  13. Sasaki, S. I.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc. Perkin Trans. 2 2001, 2309-2313
  14. Xie, H.; Yi, S.; Wu, S. J. Chem. Soc., Perkin Trans. 2 1999, 2751-2754
  15. Kubo, Y.; Ishihara, S.; Tsukahara, M.; Tokita, S. J. Chem. Soc., Perkin Trans. 2 2002, 1455-1460
  16. Kubo, Y.; Kato, M.; Misawa, Y.; Tokita, S. Tetrahedron Letters 2004, 45, 3769-3773 https://doi.org/10.1016/j.tetlet.2004.03.076
  17. Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654
  18. Nishizawa, S.; Cui, Y. Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc. Perkin Trans. 2 2002, 866-870
  19. Yeo, W. S.; Hong, J. I. Tetrahedron Letters 1998, 39, 3769-3772 https://doi.org/10.1016/S0040-4039(98)00612-1
  20. Yeo, W. S.; Hong, J. I. Tetrahedron Letters 1998, 39, 8137-8140 https://doi.org/10.1016/S0040-4039(98)01806-1
  21. Lecher, H. Z.; Gubernator, K. J. Am. Chem. Soc. 1953, 75, 1087-1092 https://doi.org/10.1021/ja01101a023
  22. Kessler, H. Angew. Chem. Internat. Edit. 1970, 9, 219-235 https://doi.org/10.1002/anie.197002191
  23. Kessler, H. Tetrahedron 1974, 30, 1861-1870 https://doi.org/10.1016/S0040-4020(01)97319-3
  24. Prevorsek, D. C.; J. Phys. Chem. 1962, 66, 769-778 https://doi.org/10.1021/j100811a001
  25. Kessler, H.; Kalinowski, H. O. Angew. Chem. Internat. Edit. 1970, 9, 641-642 https://doi.org/10.1002/anie.197006411
  26. Kim, W.; Lee, H. J.; Choi, Y. S.; Choi, J. H.; Yoon, C. J. J. Chem. Soc., Faraday Trans 1998, 94, 2663-2668 https://doi.org/10.1039/a803947j
  27. Quinonero, D.; Frontera, A.; Capo, M.; Ballester, P.; Suner, G. A.; Garau, C.; Deya, P. M. New J. Chem. 2001, 259-261
  28. Fischer, G. Chem. Soc. Rev. 2000, 29, 119-127 https://doi.org/10.1039/a803742f
  29. Taha, A. N.; True, N. S. J. Phys. Chem. A 2000, 104, 2985-2993 https://doi.org/10.1021/jp993915c
  30. Axe, F. U.; Renugopalakrishnan, V.; Hagler, A. T. J. Chem. Research (S) 1998, 1
  31. Vaara, J.; Kaski, J.; Jokisaasi, J.; Diehl, P. J. Phys. Chem. A 1997, 101, 5069-5081 https://doi.org/10.1021/jp970287v
  32. Licea, R. Q.; Valladares, J. F. C.; Quintero, A. C.; Padilla, C. R.; Guerra, R. T.; Flores, R. G.; Waksman, N. Molecules 2002, 7, 662-673 https://doi.org/10.3390/70800662
  33. Bonacorso, H. G.; Caro, M. S. B.; Zanatta, N.; Martins, A. P. J. Braz. Chem. Soc. 1992, 3, 77-79 https://doi.org/10.5935/0103-5053.19920015
  34. Ren, J.; Cai, X. H.; Fan, H. F.; Cao, J. X.; Liao, T. G.; Luo, X. D.; Zhu, H. J. Journal of Molecular Structure: Theochem 2008, 870, 72-76 https://doi.org/10.1016/j.theochem.2008.09.006
  35. Eliel, E. L.; Hofer, O. J. Am. Chem. Soc. 1973, 8041-8045
  36. Konopacka, A.; Kalenik, J.; Pawelka, Z. Journal of Molecular Structure 2004, 705, 75-79 https://doi.org/10.1016/j.molstruc.2004.05.032
  37. Ingold, K. U.; Taylor, D. R. Can. J. Chem. 1961, 39, 481-487 https://doi.org/10.1139/v61-057
  38. Eftink, M. R. Methods in Enzymology 1997, 278, 221-257 https://doi.org/10.1016/S0076-6879(97)78013-3
  39. Cannon, W. R.; Madura, J. D.; Thummel, R. P.; McCammon, J. A. J. Am. Chem. Soc. 1993, 115, 879-884 https://doi.org/10.1021/ja00056a009
  40. Gunnlaugsson, T.; Ali, H. D. P.; Glynn, M.; Kruger, P. E.; Hussey, G. M.; Pfeffer, F. M.; Santos, C. M. G. D.; Tierney, J. Journal of Fluorescence 2005, 15, 287-299 https://doi.org/10.1007/s10895-005-2627-y

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