Browse > Article
http://dx.doi.org/10.5322/JESI.2016.25.9.1283

Synthesis and Fluorescence Properties of New Rhodamine 6G Derivarives Containing Hydroxy Coumarin Moiety  

Park, Seong Ho (Department of Chemistry, Daegu University)
Chang, Seung Hyun (Department of Chemistry, Daegu University)
Publication Information
Journal of Environmental Science International / v.25, no.9, 2016 , pp. 1283-1288 More about this Journal
Abstract
In this study, we synthesized fluorescent sensors from rhodamine 6G derivatives and hydroxy coumarin. The synthetic routes to the rhodamine 6G derivatives containing hydroxy coumarin are shown in Fig. 1. Two derivatives were synthesized through Schiff base reactions. The structures of the new compounds were confirmed by melting point, $^1H$-NMR, and GC-MS analyses. The compounds were found to selectively bind to tin ($Sn^{2+}$) ion by fluorescence titration using various metal cations. Longer carbon chains gave more sensitivity. $Sn^{2+}$ ions exhibited the strongest fluorescence among the nime ions. The binding analysis using Job plots suggested that compounds form 1:1 complexes with the $Sn^{2+}$ ions.
Keywords
Rhodamine 6G; Coumarin; Fluorescence; Chemosensor;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Ahamed, B. N., Ghosh, P., 2011, An integrated system of pyrene and rhodamine-6G for selective colormetric and fluorometric sensing of mercury(II), Inorganica Chimica Acta, 372, 100-107.   DOI
2 Bao, X., Cao, X., Nie, X., Jin, Y., Zhou, B., 2014, RBAP, a rhodamine b-based derivative: Synthesis, crystal structure analysis, Molecular simulation, and its application as a selective fluorescent chemical sensor for $Sn^{2+}$, Molecules, 19, 7817-7831.   DOI
3 Beija, M., Afonso, C. A. M., Martinho, J. M. G., 2009, Synthesis and applications of rhodamine derivatives as fluorescent probes, Chem. Soc. Rev., 38, 2410-2433.   DOI
4 Cao, L., Jia, C., Zhang, Q., Wang, N., Xue, Y., Du, D., 2014, A highly selective fluorescence turn-on detection of $Al^{3+}$ and $Ca^{2+}$ based on a coumarin-modified rhodamine derivative, Tetrahedron Letters, 55, 4062-4066.   DOI
5 Huang, C. Y., 1982, Determination of binding stoichiometry by the continuous variation method: The job plot, Methods in Enzymology, 87, 509-525.
6 Huang, Z. B., Chang, S. H., 2005, Synthesis and characterization of novel ionophores of doublearmed penta-crown ethers, Tetrahedron Lett., 46, 5351-5355.   DOI
7 Huang, Z. B., Kang, T. J., Chang, S. H., 2005, The synthesis of unique structures of tetra-crown ethers through Michael addition, Tetrahedron Lett., 46, 3461-3464.   DOI
8 Jagtap, A. R., Satam, V. S., Rajule, R. N., Kanetkar, V. R., 2001, Synthesis of highly fluorescent coumarinyl chalcones derived from 8-acetyl-1,4-diethyl-1,2,3,4-tetrahydr o-7H-pyrano[2,3-g]quinoxalin-7-one and their spectral characteristics, Dyes and Pigments, 91, 20-25.
9 Kim, D. S., 2012, A study on the efficacy of the coumarine derivatives with anti-inflammatory activity in the trifoliate orange extract, J. of Korean Oil Chemists Soc., 29, 609-616.
10 Lee, K.-S., Kim, H.-J., Kim, G.-H., Shin, I.-J., Hong, J.-I., 2008, Fluorescent chemodosimeter for selective detection of cyanide in water, Org. Lett., 10, 49-51.   DOI
11 Ozkutuk, M., Ipek, E., Aydiner, B., Mamas, S., Seferoglu, Z., 2016, Synthesis, spectroscopic, thermal and electrochemical studies on thiazolyl azo based disperse dyes bearing coumarin, Journal of Molecular Structure, 1108, 521-532.   DOI
12 Yan, M. H., Li, T. R., Yang, Z. Y., 2011, A novel coumarin schiff-base as a Zn(II) ion fluorescent sensor, Inor. Chem. Comm., 14, 463-465.   DOI
13 Rojas, E., Herrera, L.-A., Poirier, L.-A., Ostrosky-Wegman, P., 1999, Are metals dietary carcinogens?, Mutation Research, 443, 157-181.   DOI
14 Chen, X., Pradhan, T., Wang, F., Kim, J. S., Yoon, J. Y., 2012, Fluorescent chemosensors based on spiroringopening of xanthenes and related derivatives, Chem. rev., 112, 1910-1956.   DOI
15 Viau, C. M., Guecheva, T. N., Sousa, F. G., Pungartnik, C., Brendel, M., Saffi, J., Henriques, J. A. P., 2009, $SnCl_2$-induced DNA damage and repair inhibition of MMS-caused lesions in V79 Chinese hamster fibroblasts, Arch Toxicol, 83, 769-775.   DOI
16 Wei, T.-B., Zhang, P., Shi, B.-B., Chen, P., Lin, Q., Liu, J., Zhang, Y.-M., 2013, A highly selective chemosensor for colorimetric detection of $Fe^{3+}$ and fluorescence turn-on response of $Zn^{2+}$, Dyes and Pigment, 97, 297-302.   DOI
17 Yi, C., Song, B., Tian, W., Cui, X., Qi, Q., Jiang, W., Qi, Z., Sun, Y., 2014, Fluorescent sensor of fluorene derivatives having phosphonic acid as a fluorogenic ionophore: Synthesis and static quenched properties for Fe(III), Tetrahedron Letters, 55, 5119-5123.   DOI
18 Zhang, X., Sumiya, S., Shiraishi, Y., Hirai, T., 2009, Effects of alkyl chain length on Cu(II)-selective green fluorescence of rhodamine-diacetic acid conjugates, Journal of Photochemistry and Photobiology A. Chemistry, 205, 215-220.   DOI