A pyrenyl-appended triazole-based calix[4]arene as a fluorescent sensor for iodide ion

Bulletin of the Korean Chemical Society

Volumn 31, Issue 3, 2010, Pages 624-629

  Kim, Jong Seung ^a   Park, Sun Young ^a   Kim, Sang Hoon ^a   Thuéry, Pierre ^b   Souane, Rachid ^c   Matthews, Susan E ^d   Vicens, Jacques ^c  

^a Korea University   (South Korea)

^b CNRS UMR 3299   (France)

^c UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^d UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

1,2,3 triazole; Anion sensing; Calixarenes; Fluorescent sensors; Iodide

Indexed keywords

ANION SENSING; CALIX[4]ARENES; CALIXARENES; CHEMOSENSOR; COMPLEX RATIO; FLUORESCENT SENSORS; IODIDE ION; RATIOMETRIC;

NEGATIVE IONS; NITROGEN COMPOUNDS; PHENOLS; SENSORS; SYNTHESIS (CHEMICAL);

FLUORESCENCE;

EID: 77951837568     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.03.624     Document Type: Article

References (89)

1. (a) Wygladacz, K.; Bakker, E. Analyst 2007, 132, 268 and references in.
2. (b) Butler, E. C. V. Trends Anal. Chem. 1996, 15, 45.
3. (c) Jayaraman, S.; Teiltler, L.; Skalski, B.; Verkman, A. S. Am. J. Physiol. Cell Physiol. 1999, 277, 1008.
4. Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302.
5. Books, special issues, and reviews on fluorescent chemosensors. (a) Czarnik, A. W. Chem. Biol. 1995, 2, 423.
6. (b) Chemosensors for Ion and Molecule Recognition. NATO ASI Series; Desvergnes, J. P., Czarnik, A. W., Eds., Kluwer Academic: Dordrecht, 1997.
7. (c) 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.
8. (d) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
9. (e) Gale, P. A. Coord. Chem. Rev. 2000, 199, 181.
10. (f) Fabrizzi, L. Ed., Luminescent Sensors; Coord. Chem. Rev. 2000, 205, 1.
11. (g) Kuswandi, B. Jurnal ILMU DASRA 2000, 1, 18.
12. (h) Bren, V. A. Russ. Chem. Rev. 2001, 70, 1017.
13. (i) Gale, P. A. Coord. Chem. Rev. 2001, 213, 79.
14. (j) Valeur, B. Molecular Fluorescence; Wiley-VCH: Weinheim, 2002.
15. (k) Diamond, D.; Nolan, K. Anal. Chem. 2001, 73, 22A-29A.
16. (l) Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. Engl. 2001, 40, 486.
17. (m) Ludwig, R.; Dzung, N. T. K. Sensors 2002, 2, 397.
18. (n) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.
19. (o) Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 61, 8551.
20. (p) Dallali, N.; Darabi, A.; Agrawal, Y. K. Rev. Anal. Chem. 2005, 24, 263.
21. (q) Amendola, V.; Fabbrizzi, I.; Forti, F.; Pallavicini, P.; Poggi, A.; Sacchi, D.; Tagleitti, A. Coord. Chem. Rev. 2006, 250, 273.
22. (r) Mancin, F.; Rampazzo, E.; Tecilla, P.; Tonellato, U. Chem. Eur. J. 2006, 12, 1844.
23. (s) Kungwandi, B.; Nurima N.; Verboom, W.; Reinhoudt, D. N. Sensors 2006, 6, 978.
24. (t) Mancin, F.; Rampazzo, E.; Tecilla, P.; Tonallato, U. Chem. Eur. J. 2006, 12, 1844.
25. (u) Valeur, B.; Leray, I. Inorg. Chem. Acta 2007, 360, 765.
26. (v) Löhr, H.-G., Vögtle, F. Acc. Chem. Res. 1985, 18, 65.
27. (w) Yang, X.-F.; Guo, X.-Q.; Zhao, Y.-B. Talanta 2002, 57, 883.
28. (x) Zhu, L.; Anslyn, E. V. Angew. Chem. Int. Ed. 2006, 45, 1190.
29. (y) Anslyn, E. V. J. Org. Chem. 2007, 72, 687.
30. (z) Bell, T. W.; Hext, N. M. Chem. Soc. Rev. 2004, 33, 589.
31. (α) Nohta, H.; Satozono, H.; Koiso, K.; Yoshida, H.; Ishida, J.; Yamaguchi, M. Anal. Chem. 2000, 72, 4199.
32. (β) Okamoto, A.; Ichiba, T.; Saito, I. J. Am. Chem. Soc. 2004, 126, 8364.
33. (χ) Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465.
34. Review articles on anions sensing. (a) Kim, S. K.; Lee, D. H.; Hong, J.-I.; Yoon, J. Acc. Chem. Res. 2009, 42, 23.
35. (b) Gale, P. A. Chem. Commun. 2008, 4525.
36. (c) Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.
37. (d) Anslyn, E. V. J. Org. Chem. 2007, 72, 687.
38. (e) Gunnlaugsson, T.; Ali, P. H. D. ; Glynn, M.; Kruger, P. E.; Hussey G. M.; Pfeffer, F. M.; Martinez-Manez, R.; Sancemon, F. J. Fluor. 2005, 15, 267.
39. (f) dos Santos, C. M. G.; Tierney, J. J. Fluor. 2005, 15, 287.
40. (g) Schmidtchen, F. P. Top. Curr. Chem. 2005, 255, 1.
41. (h) Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. 2001, 40, 486.
42. (i) Geddes, C. D. Meas. Sci. Technol. 2001, 12, R53.
43. (j) Fabbrizzi, L.; Lichelli, M.; Rabaioli, G.; Taglietti, A. Coord. Chem. Rev. 2000, 205, 85.
44. (k) Robertson, A.; Shinkai, S. Coord. Chem. Rev. 2000, 205, 157.
45. Singh, N.; Jang, D. O. Org. Lett. 2007, 9, 1991.
46. Ming, Y.; Hai, L.; Huakuan, L. Supra. Chem. 2008, 20, 357.
47. Vetrichelvan, M.; Nagarajan, R.; Valiyaveettil, S. Macromolecules 2006, 39, 8303.
48. dos Santos, C. M. G.; Glynn, M.; McCabe, T.; de Melo, J. S. S.; Burrows, H. D.; Gunnlaugsson, T. Supra. Chem. 2008, 20, 407.
49. Singh, N.; Jung, H. J.; Jang, D. O. Tetrahedron Lett. 2009, 50, 71.
50. Lin, W.; Yuan, L.; Cao, X.; Chen, B.; Feng, Y. Sensors and Actuators B: Chemical 2009, 138, 637.
51. (a) Quinlan, E.; Matthews, S. E.; Gunnlaugsson, T. J. Org. Chem. 2007, 72, 7497.
52. (b) Quinlan, E.; Matthews, S. E.; Gunnlaugsson, T. Tetrahedron Lett. 2006, 47, 9333.
53. (c) Evans, A. J.; Matthews, S. E.; Cowley, A. R.; Beer, P. D. Dalton Trans. 2003, 4644.
54. (d) Kim, J. S.; Jung, H. S.; Kim, H. J.; Vicens, J. Tetrahedron Lett. 2009, 50, 983.
55. (e) Kim, J. S.; Kim, S. H.; Kim, H. J.; Lee, Y. O.; Vicens, J. Tetrahedron Lett. 2006, 47, 4373-4377.
56. (a) Matthews, S. E.; Beer, P. D. Supramolecular Chemistry 2006, 17, 411.
57. (b) Matthews, S. E.; Beer, P. D. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds., Kluwer: Dordrecht, Holland, 2001.
58. Tornøe, C. W.; Christensen C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
59. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
60. Huisgen, R.; Szeimies, G.; Mobius, L. Chem. Ber. 1967, 100, 2494.
61. (a) Lutz, J-F. Angew. Chem. Int. Ed. 2007, 46, 1018. (b) Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249.
62. (c) Angell, Y. L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674.
63. (d) Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1369.
64. (a) Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Organic Lett. 2004, 6, 2853.
65. (b) Liu, D.; Gao, W.; Dai, Q.; Zhang, X. Org. Lett. 2005, 7, 4907
66. (c) Dai, Q.; Gao, W.; Liu, D.; Kapes, L. M.; Zhang, X. J. Org. Chem. 2006, 71, 3928.
67. (d) Bastero, A.; Font, D.; Pericàs, M. A. J. Org. Chem. 2007, 72, 2460.
68. (a) Ornelas, C.; Ruis Aranzaes, J.; Cloutet, E.; Alves, S.; Astruc, D. Angew. Chem. Int. Ed. 2007, 46, 872.
69. (b) Ornelas, C.; Ruis Aranzaes, J.; Salmon, L.; Astruc, D. Chem. Eur. J. 2008, 14, 50.
70. (c) Huang, S.; Clark, R. J.; Zhu, L. Org. Lett. 2007, 9, 4999.
71. (d) David, O.; Maisonneuve, S.; Xie, J. Tetrahedron Lett. 2007, 48, 6527.
72. Park, S-Y.; Yoon, J.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J. J. Org. Chem. 2008, 73, 8212.
73. (a) Chang, K-C.; Su, I-H.; Lee, G-H.; Chung, W-S. Tetrahedron Lett. 2007, 48, 7274.
74. (b) Chang, K-C.; Su, I-H.; Senthilvelan, A.; Chung, W-S. Org. Lett. 2007, 9, 3363.
75. (c) Colasson, B.; Save, M.; Milko, P.; Roithová, J.; Schröder, D.; Reinaud, O. Org. Lett. 2007, 9, 4987.
76. (d) Zhan, J.; Tian, D.; Li, H. New J. Chem. 2009, 33, 725.
77. Tzadka (Bulkhatsev) E.; Goldberg, I.; Vigalok, A. Chem. Comm. 2009, 2041.
78. Horne, W. S.; Yadav, M. K.; Stout, C. D.; Ghadiri, M. R. J. Amer. Chem. Soc. 2004, 126, 15366.
79. Jurwarker, H.; Lenhardt, J. M.; Pham, D. M.; Craig, S. L. Angew. Chem. Int. Ed. 2008, 47, 3740.
80. Kumar, A.; Pandey, P. S. Org. Lett. 2008, 10, 165.
81. Morales-Sanfrutos, J.; Ortega-Muñoz, M.; Lopez-Jaramillo, J.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F. J. Org. Chem. 2008, 73, 7768.
82. (a) Li, Y.; Flood, A. H. Angew. Chem. Int. Ed. 2008, 47, 2649.
83. (b) Li, Y.; Flood, A. H. J. Am. Chem. Soc. 2008, 130, 12111.
84. Ornelas, C.; Ruiz Aranzaes, J.; Cluotet, E.; Alves, S.; Astruc, D. Angew. Chem. Int. Ed. 2007, 46, 872.
85. Asfari, Z.; Bilyk, A.; Bond, C.; Harrowfield, J. M.; Koutsantonis, G. A.; Lengkeek, N.; Mocerino, M.; Skelton, B. W.; Sobolev, B. N.; Strano, S.; Vicens, J.; White, A. H. Org. Biomol. Chem. 2004, 2, 387.
86. Chetcuti, M. J.; Devoille, A. M. J.; Ben Othman, A.; Souane, R.; Thuéry, P.; Vicens, J. Dalton Trans. 2009, 16, 2999.
87. Hooft, R. W. W. COLLECT; Nonius BV: Delft, The Netherlands, 1998.
88. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
89. Sheldrick, G. M. Acta Crystallogr., Section A 2008, 64, 112.