DOI QR코드

DOI QR Code

Synthesis of Novel Fluorescent Dye Based on Fluorescein

  • Hwang, Ji-Yong (Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University) ;
  • Son, Young-A (Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University)
  • Received : 2014.07.01
  • Accepted : 2014.09.16
  • Published : 2014.09.27

Abstract

The functional materials have been developed as a promising research topic toward the end uses for organic materials and applications. In this study, fluorescein based dye was synthesized by three step reaction. We have designed and synthesized the colorimetric dye through the reactions of fluorescein and methoxy group and ethylene diamine and squaric acid. The structure of the non-fluorescent spirolactam was elucidated by $^1H$-NMR, LC-Mass and FT-IR analyzes. Further studies are in progress to understand the effects of various substituent during the recognition process and to develop fluorescein based sensors for cations or anions.

Keywords

References

  1. D. Wild, "The Immunoassay Handbook", Stockton Press, New York, 1994.
  2. X. Chen, T. Pradhan, F. Wang, J. S. Kim, and J. Yoon, Fluorescent Chemosensors based on Spiroringopening of Xanthenes and Realated Derivatives, Chemical Society Reviews, 112, 1910(2012). https://doi.org/10.1021/cr200201z
  3. R. P. Haugland, "Handbook of Fluorescent Probes and Research Chemicals 6th ed", Molecular Probes, Eugene, OR, 1996.
  4. M. Adamczyk and J. Grote, Synthesis of Novel Spirolactams by Reaction of Fluorescein Methyl Ester with Amines, Tetrahedron Letters, 41, 807(2000). https://doi.org/10.1016/S0040-4039(99)02197-8
  5. U. Anthoni, C. Christophersen, P. Nielsen, A. Puschl, and K. Schaumburg, Structure of Red and Orange Fluorescein, Structural Chemitry, 3, 161(1995).
  6. R. Marekuszewski and H. Diehl, The Infrared Spectra and Structures of the Three Solid forms of Fluorescein and Related Compounds, Talanta, 27, 937(1980). https://doi.org/10.1016/0039-9140(80)80125-1
  7. G. Wei, L. Wang, J. Jiao, J. Hou, Y. Cheng, and C. Zhu, $Cu^{2+}$ triggered Fluorescence Sensor based on Fluorescein Derivative for $Pd^{2+}$ Detection, Tetrahedron Letters, 53, 3459(2012). https://doi.org/10.1016/j.tetlet.2012.04.108
  8. V. Dujols, F. Ford, and A. W. Czarmik, A Long-wavelength Fluorescent Chemodosimeter Selective for Cu(II) Ion in Water, J. of the American Chemical Society, 119, 7386(1997). https://doi.org/10.1021/ja971221g
  9. F. A. Guerri, A. Costela, J. M. Figuera, F. Florido, and R. Sastre, Laser Action from Rhodamine 6G-doped Poly(2-hydroxyethyl methacrylate) Matrices with Different crosslinking Degrees, Chemical Physics Letters, 209, 352(1993). https://doi.org/10.1016/0009-2614(93)80029-O
  10. M. Goncalves and T. Sameiro, Fluorescent Labeling of Biomolecules with Organic Probes, Chemical Society Reviews, 109, 190(2009). https://doi.org/10.1021/cr0783840
  11. W. Feuerstein and M. Dutoit, Ueber Das Phtaleïn des Oxyhydrochinons, Berichte der Deutschen Chemischen Gesellschaft, 34, 2637(1901). https://doi.org/10.1002/cber.190103402216
  12. L. Jiang, L. Wang, M. Guo, G. Yin, and R. Y. Wang, Fluorescence Turn-on of Easily Prepared Fluorescein Derivatives by Zinc Cation in Water and Living Cells, Sensors and Actuators B, 156, 825(2011). https://doi.org/10.1016/j.snb.2011.02.048
  13. M. Adamczyk, J. Grote, and J. A. Moore, Chemoenzymatic Synthesis of 3'-O-(carboxyalkyl) Fluorescein Labels, Bioconjugate Chemistry, 10, 544(1999). https://doi.org/10.1021/bc990009u
  14. X. Chen and H. Ma, A Selective Fluorescence-on Reaction of Spiro Form Fluorescein Hydrazide with Cu(II), Analytica Chimica Acta, 575, 217(2006). https://doi.org/10.1016/j.aca.2006.05.097
  15. X. F. Yang, D. B. Wu, and H. Li, Sensitive Determination of Cobalt(II) using a Spiro Fluorescein Hydrazide as a Chemiluminogenic Reagent, Microchimica Acta, 149, 123(2005). https://doi.org/10.1007/s00604-004-0285-4
  16. X. F. Yang, Y. Li, and Q. Bai, A Highly Selective and Sensitive Fluorescein-based Chemodosimeter for $Hg^{2+}$ Ionsinaqueousmedia, Analytica Chimica Acta, 584, 95(2007). https://doi.org/10.1016/j.aca.2006.11.015
  17. C. Prabhakar, K. Bhanuprakash, V. J. Rao, M. Balamuralikrishna, and D. N. Rao, Third Order Nonlinear Optical Properties of Squaraine Dyes having Absorption below 500 nm: a Combined Experimental and Theoretical Investigation of Closed Shell Oxyallyl Derivatives, J. of Physical Chemistry C, 114, 6077(2010). https://doi.org/10.1021/jp908475n
  18. F. Yan, M. Wang, D. Cao, N. Yang, Y. Fu, and L. Chen, New Fluorescent and Colorimetric Chemosensors based on the Rhodamine Detection of $Hg^{2+}$ and $Al^{3+}$ and Application of Imaging in Living Cells, Dyes and Pigments, 98, 42(2013). https://doi.org/10.1016/j.dyepig.2013.02.002
  19. D. Wu, W. Huang, C. Duan, Z. Lin, and Q. Meng, Highly Sensitive Fluorescent Probe for Selective Detection of $Hg^{2+}$ in DMF Aqueous Media, Inorganic Chemistry, 46, 1538(2007). https://doi.org/10.1021/ic062274e
  20. H. G. Kim, S. Wang, and Y. A. Son, Synthesis and Properties of Novel Rhodamine 6G Fluorescent Dye Compound, Textile Coloration and Finishing (J. of Korea Soc. Dyers and Finishers), 24, 153(2012). https://doi.org/10.5764/TCF.2012.24.3.153
  21. H. G. Kim, A. R. Boddu, and Y. A. Son, Electrochemical Study for 1,3-bisdicyanovinylindane, Textile Coloration and Finishing(J. of Korea Soc. Dyers and Finishers), 25, 89(2013). https://doi.org/10.5764/TCF.2013.25.2.89