Journal of Environmental Science International (한국환경과학회지)

The Korean Environmental Sciences Society (한국환경과학회)
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Synthesis and Fluorescence Properties of New Rhodamine 6G Derivarives Containing Hydroxy Coumarin Moiety

새로운 로다민 6G 하이드록시 쿠마린 유도체의 합성과 형광특성

  • Received : 2016.08.08
  • Accepted : 2016.09.12
  • Published : 2016.09.30
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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.

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References

  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. https://doi.org/10.1016/j.ica.2011.01.071
  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. https://doi.org/10.3390/molecules19067817
  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. https://doi.org/10.1039/b901612k
  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. https://doi.org/10.1016/j.tetlet.2014.06.015
  5. 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. https://doi.org/10.1021/cr200201z
  6. Huang, C. Y., 1982, Determination of binding stoichiometry by the continuous variation method: The job plot, Methods in Enzymology, 87, 509-525.
  7. Huang, Z. B., Chang, S. H., 2005, Synthesis and characterization of novel ionophores of doublearmed penta-crown ethers, Tetrahedron Lett., 46, 5351-5355. https://doi.org/10.1016/j.tetlet.2005.06.006
  8. 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. https://doi.org/10.1016/j.tetlet.2005.03.120
  9. 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.
  10. 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.
  11. 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. https://doi.org/10.1021/ol7025763
  12. 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. https://doi.org/10.1016/j.molstruc.2015.12.032
  13. Rojas, E., Herrera, L.-A., Poirier, L.-A., Ostrosky-Wegman, P., 1999, Are metals dietary carcinogens?, Mutation Research, 443, 157-181. https://doi.org/10.1016/S1383-5742(99)00018-6
  14. 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. https://doi.org/10.1007/s00204-009-0409-z
  15. 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. https://doi.org/10.1016/j.dyepig.2012.12.025
  16. 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. https://doi.org/10.1016/j.tetlet.2014.05.105
  17. 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. https://doi.org/10.1016/j.inoche.2010.12.027
  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. https://doi.org/10.1016/j.jphotochem.2009.05.006