Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.5.1429

A Carbazole-Attached NO2S2-Macrocycle Exhibiting Hg2+ and Cu2+ Selectivity  

Lee, Seul-Gi (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Kang, Eun-Ju (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Lee, Shim Sung (Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.5, 2013 , pp. 1429-1434 More about this Journal
Abstract
A synthesis and cation-induced fluorescent behavior of the carbazole-attached $NO_2S_2$-macrocycle (L) is described and structurally characterized by single crystal X-ray analysis. The photoluminescence spectrum of L in 80% $CH_3CN/CH_2Cl_2$ displays a peak maximum at 431 nm (blue emission). In the metal-induced fluorometric experiment, L showed a drastic chelation-enhanced fluorescence quenching (CHEQ) effect only with $Hg^{2+}$ and $Cu^{2+}$. In ESI-mass study, a 1:1 stoichiometry for complexation of L with $Hg^{2+}$ was confirmed, suggesting the unique sensing behavior of the proposed ligand L due to the selective complexation affinity for $Hg^{2+}$. The observed results indicate that L is a promising turn-off type fluoroionophore for $Hg^{2+}$ and $Cu^{2+}$ detections. Additionally, the $Ag^+$ complex of the precursor macrocycle was prepared and its solid structure was crystallographically characterized.
Keywords
Carbazole-attached macrocycle; Fluoroionophore; Mercury(II); Copper(II); X-ray crystal structure;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
연도 인용수 순위
1 Guney, O.; Cebeci, F. C. J. Appl. Polym. Sci. 2010, 117, 2373.   DOI   ScienceOn
2 Danjou, P.-E.; Lyskawa, J.; Delattre, F.; Becuwe, M.; Woisel, P.; Ruellan, S.; Fourmentin, S.; Cazier-Dennin, F. Sens. Actuators, B 2012, 171, 1022.
3 Lee, S. J.; Lee, S. S.; Lee, J. Y.; Jung, J. H. Chem. Mater. 2006, 18, 4713.   DOI   ScienceOn
4 Lee, S. J.; Lee, S. S.; Jeong, I. Y.; Lee, J. Y.; Jung, J. H. Tetrahedron Lett. 2007, 48, 393.   DOI   ScienceOn
5 Kang, Y.; Moon, S.-T.; Park, S.; Kim, J.; Lee, S. S.; Park, K.-M. Bull. Korean Chem. Soc. 2007, 28, 873.   DOI   ScienceOn
6 Lee, H.; Lee, S. S. Org. Lett. 2009, 11, 1393.   DOI   ScienceOn
7 Lee, Y. H.; Lee, S. S. J. Incl. Phenom. 2001, 39, 235.   DOI   ScienceOn
8 Kim, H. J.; Song, M. R.; Lee, S. Y.; Lee, J. Y.; Lee, S. S. Eur. J. Inorg. Chem. 2008, 3532.
9 Bruker, SMART and SAINT, Area Detector Control and Integ-ration Software version 6.22; Bruker AXS Inc.: Madison, WI, 2001.
10 Bruker, SHELXTL-PC version 6.22: Program for Solution and Refinement of Crystal Structures; Bruker AXS Inc.: Madison, Wisconsin, U.S.A. 2008.
11 Bruker, SADABS version 6.10: Empirical Absorption and Correction Software; Bruker AXS Inc.: Madison, Wisconsin, U.S.A. 1999.
12 Gervat, S.; Leonel, E.; Barraud, J.-Y.; Ratovelomanana, V. Tetrahedron Lett. 1993, 34, 2115.   DOI   ScienceOn
13 Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030.   DOI   ScienceOn
14 de Groot, B.; Loeb, S. J.; Shimizu, G. K. H. Inorg. Chem. 1994, 33, 2663.   DOI   ScienceOn
15 Constable, E. C.; King, A. C.; Raithby, P. R. Polyhedron 1998, 17, 4275.   DOI   ScienceOn
16 Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecule Recognition; American Chemical Society: Washington, DC, 1993.
17 Desvergne, J. P.; Czarnik, A. W. Chemosensors of Ion and Molecular Recognition; NATO ASI Series; Kluwer: Dordrecht, The Netherlands, 1997.
18 Valeur, B. Molecular Fluorescence: Principles and Applications; Wiley-VCH: New York, 2001.
19 Martínez-Máñez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.   DOI   ScienceOn
20 Hudson, Z. M.; Wang, S. Acc. Chem. Res. 2009, 42, 1584.   DOI   ScienceOn
21 Quang, D. T.; Kim, J. S. Chem. Rev. 2010, 110, 6280.   DOI   ScienceOn
22 Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. Angew. Chem. Int. Ed. 2000, 39, 1052.   DOI
23 Sancenon, F; Martinez-Manez, R.; Soto, J. Angew. Chem. Int. Ed. 2002, 41, 1416.   DOI
24 Park, C. S.; Lee, J. Y.; Kang, E.-J.; Lee, J.-E.; Lee, S. S. Tetrahedron Lett. 2009, 50, 671.   DOI   ScienceOn
25 Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302.   DOI   ScienceOn
26 Basu, G.; Kubasik, M.; Anglos, D.; Kuki, A. J. Phys. Chem. 1993, 97, 3956.   DOI   ScienceOn
27 Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.   DOI   ScienceOn
28 Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101.   DOI   ScienceOn
29 Kavarnos, G.; Cole, T.; Scribe, P.; Dalton, J. C.; Turro, N. J. J. Am. Chem. Soc. 1971, 93, 1032.   DOI
30 Basu, G.; Kubasik, M.; Anglos, D.; Secor, G.; Kuki, A. J. Am. Chem. Soc. 1990, 112, 9410.   DOI
31 Lee, S. Y.; Park, S.; Kim, H. J.; Jung, J. H.; Lee, S. S. Inorg. Chem. 2008, 47, 1913.   DOI   ScienceOn
32 de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; NcCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.   DOI   ScienceOn
33 de Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev. 2000, 205, 41.   DOI   ScienceOn
34 Amendola, V.; Rabbrizzi, L.; Lincchelli, M.; Mangano, C.; Pallavicini, P.; Parodi, L.; Poggi, A. Coord. Chem. Rev. 1999, 190, 649.
35 (a) Jin, Y.; Yoon, I.; Seo, J.; Lee, J.-E.; Moon, S.-T.; Kim, J.; Han, S. W.; Park, K.-M.; Lindoy, L. F.; Lee, S. S. Dalton Trans. 2005, 788.
36 Lee, J.-E.; Jin, Y.; Seo, J.; Yoon, I.; Song, M. R.; Lee, S. Y.; Park, K. M.; Lee, S. S. Bull. Korean Chem. Soc. 2006, 27, 203.   DOI   ScienceOn
37 Lee, S. J.; Jung, J. H.; Seo, J.; Yoon, I.; Park, K.-M.; Lindoy, L. F.; Lee, S. S. Org. Lett. 2006, 8, 1641.   DOI   ScienceOn
38 Lee, S. J.; Lee, J.-E.; Seo, J.; Jeong, I. Y.; Lee, S. S.; Jung, J. H. Adv. Funct. Mater. 2007, 17, 3441.   DOI   ScienceOn
39 Grabchev, I.; Chovelon, J.-M.; Bojinov, V. Polym. Adv. Technol. 2004, 15, 382.
40 Zou, Y.; Wan, M.; Sang, G.; Ye, M.; Li, Y. Adv. Funct. Mater. 2008, 18, 2724.   DOI   ScienceOn