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http://dx.doi.org/10.5764/TCF.2014.26.3.272

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)
Publication Information
Textile Coloration and Finishing / v.26, no.3, 2014 , pp. 272-276 More about this Journal
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
fluorescein; squaric acid; spiolactam; fluorescein methyl ester; xanthene dye;
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Times Cited By KSCI : 2  (Citation Analysis)
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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).   DOI   ScienceOn
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).   DOI
5 R. Marekuszewski and H. Diehl, The Infrared Spectra and Structures of the Three Solid forms of Fluorescein and Related Compounds, Talanta, 27, 937(1980).   DOI
6 M. Goncalves and T. Sameiro, Fluorescent Labeling of Biomolecules with Organic Probes, Chemical Society Reviews, 109, 190(2009).   DOI   ScienceOn
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).   DOI   ScienceOn
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).   DOI   ScienceOn
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).   DOI
10 W. Feuerstein and M. Dutoit, Ueber Das Phtaleïn des Oxyhydrochinons, Berichte der Deutschen Chemischen Gesellschaft, 34, 2637(1901).   DOI
11 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).   DOI
12 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).   DOI   ScienceOn
13 M. Adamczyk, J. Grote, and J. A. Moore, Chemoenzymatic Synthesis of 3'-O-(carboxyalkyl) Fluorescein Labels, Bioconjugate Chemistry, 10, 544(1999).   DOI
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).   DOI   ScienceOn
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).   DOI
16 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).   DOI
17 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).   DOI
18 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).   DOI   ScienceOn
19 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).   DOI   ScienceOn
20 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).   DOI
21 U. Anthoni, C. Christophersen, P. Nielsen, A. Puschl, and K. Schaumburg, Structure of Red and Orange Fluorescein, Structural Chemitry, 3, 161(1995).