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http://dx.doi.org/10.5012/bkcs.2011.32.5.1599

Fluorescence Sensing Properties of 2-(2'-Hydroxyphenyl)quinoline and Derivatives  

Helal, Aasif (Department of Applied Chemistry, Kyungpook National University)
Lee, Sang-Hoon (Department of Applied Chemistry, Kyungpook National University)
Ren, Wen Xiu (Department of Applied Chemistry, Kyungpook National University)
Cho, Chan-Sik (Department of Applied Chemistry, Kyungpook National University)
Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.5, 2011 , pp. 1599-1603 More about this Journal
Abstract
Novel chemosensors based on 2-(2'-hydroxyphenyl)quinoline were prepared and evaluated for sensing metal cations. The photophysical properties of chemosensors 1-3 were examined and their ion-selectivity was evaluated by measuring their fluorescent emission responses to alkali, alkaline earth, and transition metal ions. Chemosensors 1, 2 and 3 show ratiometric and enhanced fluorescence changes with transitional metals that are efficient fluorescence quenchers, especially 3 has a high binding constant with $Hg^{+2}$ in $CH_3CN$.
Keywords
Fluorescence; Chemosensor; Quinoline; Phenol; $Hg^{+2}$;
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1 Moon, S. Y.; Cha, N. R.; Kim, Y. H.; Chang, S.-K. J. Org. Chem. 2004, 69, 181.   DOI   ScienceOn
2 Kim, Y.-H.; Youk, J. S.; Moon, S. Y.; Choe, J.-I.; Chang, S.-K. Chem. Lett. 2004, 33, 702.   DOI   ScienceOn
3 Ghosh, P.; Bharadwaj, P. K.; Roy, J.; Ghosh, S. J. Am. Chem. Soc. 1997, 119, 11903.   DOI   ScienceOn
4 Ramachandram, B.; Samanta, A. Chem. Commun. 1997, 1037.
5 Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 14270.   DOI   ScienceOn
6 Guo, X.; Qian, X.; Jia, L. J. Am. Chem. Soc. 2004, 126, 2272.   DOI   ScienceOn
7 Davis, M. J.; Kragor, C. H.; Reddie, K. G.; Wilson, H. C.; Zhu, Y.; Dore, T. M. J. Org. Chem. 2009, 74, 1721.   DOI   ScienceOn
8 Helal, A.; Kim, H.-S. Tetrahedron Lett. 2009, 50, 5510.   DOI   ScienceOn
9 Helal, A.; Kim, S.-H.; Kim, H.-S. Tetrahedron 2010, 66, 9925.   DOI   ScienceOn
10 Helal, A.; Thao, N. T. T.; Lee, S.; Kim, H.-S.; J. Inclusion Phenom. Macrocyclic Chem. 2010, 66, 87.   DOI
11 Helal, A.; Kim, H.-S. Tetrahedron 2010, 66, 7097.   DOI   ScienceOn
12 Helal, A.; Lee, S. H.; Kim, S. H.; Kim, H.-S. Tetrahedron Lett. 2010, 51, 3531.   DOI   ScienceOn
13 Song, K. C.; Kim, J. S.; Park, S. M.; Chung, K.-C.; Ahn, S.; Chang, S.-K. Org. Lett. 2006, 8, 3413.   DOI   ScienceOn
14 Li, N.; Xu, Q.; Xia, X.; Wang, L.; Lu, J.; Wen, X. Mater. Chem. Phys. 2009, 114, 339.   DOI   ScienceOn
15 Bardez, E.; Devol, I.; Larrey, B.; Valeur, B. J. Phys. Chem. B 1997, 101, 7786.   DOI   ScienceOn
16 Han, D. Y.; Kim, J. M.; Kim, J.; Jung, H. S.; Lee, Y. H.; Zhang, J. F.; Kim, J. S. Tetrahedron Lett. 2010, 51, 1947.   DOI   ScienceOn
17 Canovese, L.; Visentin, F.; Chessa, G.; Levi, C.; Nikolov, P. Inorg. Chim. Acta 2009, 362, 3925.   DOI   ScienceOn
18 Launay, F.; Alain, V.; Destandau, E. A.; Ramos, N.; Bardez, E. A.; Baret, P.; Pierre, J.-L. New J. Chem. 2001, 25, 1269. 14.   DOI   ScienceOn
19 Cho, C. S.; Kim, B. T.; Kim, T. J.; Shim, S. C. Chem. Commun. 2001, 2576.
20 Keck, J.; Kramer, H. E. A.; Port, H.; Hirsch, T.; Fischer, P.; Rytz, G. J. Phys. Chem. 1996, 100, 14468.   DOI   ScienceOn
21 Shults, M. D.; Imperiali, B. J. Am. Chem. Soc. 2003, 125, 14248.   DOI   ScienceOn
22 Shults, M. D.; Pearce, D. A.; Imperiali, B. J. Am. Chem. Soc. 2003, 125, 10591.   DOI   ScienceOn
23 Pearce, D. A.; Jotterand, N.; Carrico, I. S.; Imperiali, B. J. Am. Chem. Soc. 2001, 123, 5160.   DOI   ScienceOn
24 Jotterand, N.; Pearce, D. A.; Imperiali, B. J. Org. Chem. 2001, 66, 3224.   DOI   ScienceOn
25 Walkup, G. K.; Imperiali, B. J. Org. Chem. 1998, 63, 6727.   DOI   ScienceOn
26 Bronson, R. T.; Montalti, M.; Prodi, L.; Zaccheroni, N.; Lamb, R. D.; Dalley, N. K.; Izatt, R. M.; Bradshaw, J. S.; Savage, P. B. Tetrahedron 2004, 60, 11139.   DOI   ScienceOn
27 Bronson, R. T.; Bradshaw, J. S.; Savage, P. B.; Fuangswasdi, S.; Lee, S. C.; Krakowiak, K. E.; Izatt, R. M. J. Org. Chem. 2001, 66, 4752.   DOI   ScienceOn
28 Prodi, L.; Montalti, M.; Zaccheroni, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. Tetrahedron Lett. 2001, 42, 2941.   DOI   ScienceOn
29 Prodi, L.; Bargossi, C.; Montalti, M.; Zaccheroni, N.; Su, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. J. Am. Chem. Soc. 2000, 122, 6769.   DOI   ScienceOn
30 Fahrni, C. J.; O'Halloran, T. V. J. Am. Chem. Soc. 1999, 121, 11448.   DOI   ScienceOn
31 Thompson, R. B. Curr. Opin. Chem. Biol. 2005, 9, 526.   DOI   ScienceOn
32 Chien, T. C.; Dias, L. G.; Arantes, G. M.; Santos, L. G. C.; Triboni, E. R.; Bastos, E. L.; Politi, M. J. J. Photochem. Photobiol. A 2008, 194, 37.   DOI   ScienceOn
33 Quang, D. T.; Kim, J. S. Chem. Rev. 2010, 110, 6280.   DOI   ScienceOn
34 Connors, K. A. Binding Constants: the Measurement of Molecular Complex Stability; Wiley: New York, 1987; pp 21-101; 339-343.
35 Zhou, Z.; Fahrni, C. J. J. Am. Chem. Soc. 2004, 126, 8862.   DOI   ScienceOn
36 Leray, I.; O'Reilly, F.; Habib Jiwan, J.-L.; Soumillion, J.-Ph.; Valeur, B. Chem. Commun. 1999, 795.
37 Young, V. G.; Quiring, H. L.; Sykes, A. K. J. Am. Chem. Soc. 1997, 119, 12477.   DOI   ScienceOn
38 Forgues, S. F.; LeBris, M. T.; Gutte, J. P.; Valuer, B. J. Phys. Chem. 1988, 92, 6233.   DOI
39 Gnuplot 4 (www.gnuplot.info).
40 Su, N.; Bradshaw, J. S.; Zhang, X. X.; Song, H.; Savage, P. B.; Xue, G.; Krakowiak, K. E.; Izatt, R. M. J. Org. Chem. 1999, 64, 8855.   DOI   ScienceOn
41 Winkler, J. K.; Bowen, C. M.; Michelet, V. J. Am. Chem. Soc. 1998, 120, 3237.   DOI   ScienceOn
42 Hayashi, M.; Ishii, M.; Hiratani, K.; Saigo, K. Tetrahedron Lett. 1998, 39, 6215.   DOI   ScienceOn
43 Baret, P.; Beguin, C. G.; Boukhalfa, H.; Caris, C.; Laulhere, J.-P.; Pierre, J.-L.; Serratrice, G. J. Am. Chem. Soc. 1995, 117, 9760.   DOI   ScienceOn
44 Zhang, J. F.; Kim, J. S. Anal. Sci. 2009, 25, 1271.   DOI   ScienceOn
45 Katzenellenbogen, J. A.; Haroutounian, S. A. Photochem. Photobiol. 1988, 47, 503.   DOI   ScienceOn
46 Swinburne, A. N.; Paterson, M. J.; Beeby, A.; Steed, J. W. Org. Biomol. Chem. 2010, 8, 1010.   DOI   ScienceOn
47 Goswami, S.; Chakrabarty, R. Tetrahedron Lett. 2009, 50, 5994.   DOI   ScienceOn
48 Zhang, D. Inorg. Chem. Commun. 2009, 12, 1255.   DOI   ScienceOn
49 Zhang, L.; Meggers, E. J. Am. Chem. Soc. 2005, 127, 74.   DOI   ScienceOn
50 Jiang, P.; Guo, Z. Coord. Chem. Rev. 2004, 248, 205.
51 Zelder, F. Z.; Brunner, J.; Kramer, R. Chem. Commun. 2004, 902.
52 Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.   DOI   ScienceOn