Browse > Article
http://dx.doi.org/10.5012/bkcs.2010.31.03.624

A Pyrenyl-Appended Triazole-Based Calix[4]arene as a Fluorescent Sensor for Iodide Ion  

Kim, Jong-Seung (Department of Chemistry, Korea University)
Park, Sun-Young (Department of Chemistry, Korea University)
Kim, Sang-Hoon (Department of Chemistry, Korea University)
Thuery, Pierre (CEA, IRAMIS, SCM, LCCEf (CNRS URA 331))
Souane, Rachid (IPHC-UdS-ECPM-CNRS)
Matthews, Susan E. (School of Chemical Sciences and Pharmacy, University of East Anglia)
Vicens, Jacques (IPHC-UdS-ECPM-CNRS)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.3, 2010 , pp. 624-629 More about this Journal
Abstract
The synthesis and evaluation of a novel calix[4]arene-based fluorescent chemosensor 1 for the detection of I. is described. The fluorescent changes observed upon addition of various anions show that 1 is selective for I. over other anions. Addition of I. results in ratiometric measurements with 1 : 1 complex ratio.
Keywords
1,2,3-Triazole; Calixarenes; Fluorescent sensors; Anion sensing; Iodide;
Citations & Related Records

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