The Study of Chemiluminescence of Acridinium Ester in Presence of Rhodamin B as a Fluorescer

Document Type : Research Article

Authors

1 Department of Chemistry, Mazandaran University, Babolsar, I.R. IRAN

2 Department of Chemistry, Islamic Azad University, Savadkooh Branch, Savadkooh, I.R. IRAN

3 Department of Biochemistry, Tarbiat Modaress University, Tehran, I.R. IRAN

4 Department of Chemistry, Razi University, Kermanshah, I.R. IRAN

Abstract

The reaction of hydrogen peroxide and  pheny -9-acridinecarboxylate in the presence of rhodamin B as a fluorophore leads to the emission of either bright blue light  or bright red light, depending on the structure of fluorescer and reaction conditions. The light emitter responsible for the Chemi Luminescence (CL) reaction is acridone and that the blue light produced with out the fluorescers is  a result of direct CL. The intensity and kinetic parameters for the CL systems were evaluated from fitting of the resulting intensity-time plots. The CL systems were investigated as concentration dependent of fluorescer, hydrogen peroxide, acridinium ester and sodium hydroxide as a catalyst.

Keywords

Main Subjects

References

[1] White E.H., Roswell D.F., Chemiluminescence of 4-Styrylphthal-Hydrazides with Crown Ether as Ionophore,  Acc. Chem. Res., 3, p. 541 (1970).
[2] White E.H., Steinmetz M.G., Miano J.D., Wildes P.D., Morland R., A Dynamic Chemiluminescent Process. Cyclic and Acyclic Pathways in the Photooxidative Decarbonylation of 5-Methylfurfural,  J. Am. Chem. Soc., 102, p. 3199 (1980).
[3] Weeks I., Sturgess M.L., Brown R.C., Woodhead J.S., Immunoassays Using Acridinium Ester, Methods  Enzymol, 133, p.366 (1986).
[4] Lehmstedt K., Wirth E., Some Ms-Acridine Derivatives, Ber. Dtsch. Chem. Ges., 61, p. 2044 (1928).
[5] Gleu K.,  PetschW., Two-Color Chemiluminescent Clock Reaction (Synthesized lucigenin), Angew. Chem., 48, p. 57 (1935).
[6] Albrecht H.O., Uber Die Chemiluminescenz Des Aminiphthalsaure Hydrazides,  J. Phys. Chem., 136,       p. 321 (1928).
[7] Barnard G., Brockelbank J.L., Kim J.B., Collins W.P., “Analytical Application of Bioluminesence and Chemiluminescence”, (Kricka, L. J., Stanley, P. E., Thorope, G. H. G., Whitehead, T. P. Eds.) Academic Press, New Yourk, p. 159 (1984).
[8] White E.H., Roswell D.F., Dupont A.C., Wilson A.A., Chemiluminescence Involving Acidic and Ambident Ion Light Emitters.The Chemiluminescence of the 9-Acridinepercarboxylate Anion, J. Am. Chem. Soc., 109, p. 5189 (1987).
[9] Tonkin S.A, Bos R., Dyson G.A., Lim K. F., Russell  R.A., Watson S.P.,  Hindson C.M., Barnett N.W., Studies on the Mechanism of the Peroxyoxalate Chemiluminescence Reaction: Part 2. Further Identification of Intermediates Using 2D EXSY 13C Nuclear Magnetic Resonance Spectroscopy,  Analytica Chimica Acta, 614 (2), p. 173 (2008).
[10] Akhavan  Tafti  H.,  Assay  Methods  Using Chemiluminescent Detection of Peroxidase, European Patent Application, 0625510 A2, (1994).
[11] Lehmstedt K., Wirth E., Uber Einige Ms-Acridi-Derivate, Chem. Ber., 61, p. 2044 (1928).
[12] Zaklika  K.A.,  Reaction  Mechanisms  in Chemiluminescence, Ph. D. Thesis, University of Sussex,UK, (1976).
[13] Deluca M.A., Mc Elroy W.D, “Bioluminesence and Chemiluminescence Methods in Enzymology”, Academic Press, Inc., Vol. 133 (1986).
[14] Campbell A.K.,  Simpson  J.S.A.,  Chemi-and Bioluminescence as an Analytical Tool in Biology, Tech Metabolic Res, B 213, p. 1 (1979).
[15] McCapra  F.,  Beheshti I.,  Kastooriranganathan  R., Ammonium Substituted Chemiluminescent Labels and Their Conjugates, and Assays There from, US Patent, 5281712 (1994). 
[16] Rieche A., Schmitz E., Dietrich P., Stickstoffhaltige Peroxyde, III. Peroxyde aus Stickstoffhaltigen Pseudobasen. Eine Methode zur Identifizierung Von Alkylhydroperoxyden, Chem. Ber., 92, p. 2239 (1959).
[17] Ball  D.L.,  Crutchfield  M.M.,  Edwards  J.O.,  The Mechanism of the Oxidation of 2-Propanol by Peroxydisulfate Ion, J. Org. Chem., 25, p. 1599 (1960).
[18] Chandross  E.A.,  Sonntag  F.I.,  A  Novel Chemiluminescent Electron-Transfer Reaction, J. Am. Chem. Soc., 86 (15), p. 3179 (1964).
[19] Mc Capra F., RichardsonD.G., The Mechanism of Chemiluminescence: A New Chemiluminescence Reaction, Tetrahedron Letters, 43, p. 3167 (1964).
[20] Burr J.G.,  “Chemi and Bioluminescence”,Marcell-Dekker,New York, p 245 (1985).
[21] Robards K., Worsfold  P.J, Analytical Applications of Liquid-Phase Chemiluminescence, Anal. Chim. Acta., 266, p. 147 (1992).
[22] Hadd A.G., Birks J.W., in R. E. Sievers (Ed), “Selective Detectors, Chemical Analysis”, Wiley, N.Y. USA  ,. 131, p. 209 (1995).
[23] Nakashima K., Abe K., Nakamura S., Wada M.,  Harada S., Kuroda N., Effects of Surfactants on Peroxyoxalate Chemiluminescence Reaction, Luminescence, 23(2), p. 86 (2008).
[24] Chaichi  M.J.,  Karami  A.R.,  Shockravi  A., Shamsipur M., Chemiluminescence Characteristics of Cumarin Derivatives as Blue Fluorescers in Peroxyoxalate-Hydrogen Peroxide System, Spectrochimica Acta part A, 59 (6), p. 1145 (2003).
[25] Givens R.S., Schowman R.L., in Birks J.W. (Ed), “Chemiluminescence and Photochemical Reaction Detection in Chromatography”, New York, VCH, Chapter 5 (1989).
[26] Orlovic M., Schowman R.L., Givens R.S., Alvarez F., Matuszewski B., Parekh N., A Simplified Model for the Dynamics of Chemiluminescence in the Oxalate-Hydrogen Peroxide System: Toward a Reaction Mechanism, J. Org. Chem., 54, p. 3606 (1989).
[27] Hadd A.G., Seeber A., Birks J.W., Kinetics of Two Pathways in Peroxyoxalate Chemiluminescenc,
J. Org. Chem.., 65, p. 2675 (2000).
[28] Hosseini M., Dehghan S., Chaichi M.J., Ganjali M.R., Norouzi P., A Study of Quenching and Enhancing Effects of Some Amino Acids on Peroxyoxalate Chemiluminescence of Rhodamine 6G, Spectrochimica Acta A, Molecular and Biomolecular Spectroscopy, 72(3), p. 484 (2009).
[29] Dye J.L., Nicely V.A., A General Purpose Curve Fitting Program for Class and Research Use, J. Chem. Edu., 48, p. 443 (1971).
[30] Zomer G., Stavenuiter J.F.C., Van Den Berg R.H., Jansen E.H.J.M., “Luminescence Techniques in Chemical and Biochemical Analysis” (Baeyens, W.R.G., De Keukeleire, D., Korkidis, K., Eds.) Marcell Dekker  Inc., p 514 (1991).
[31] Shamsipur M., Chaichi M.J., Karami A.R., A Study of Peroxyoxalate-Chemiluminescence of Acriflavine, Spectrochimica Acta part A, , 59 (3), p. 511 (2003).
[32] Hosseini M., Dehghan S., Chaichi M.J., Shamsipur M., A Study of Chemiluminescence from Reaction of Bis (2,4,6-Trichlorophenyl)Oxalate, Hydrogen Peroxide and Dithranol as Antipsoriatic Drug and its Analytical Application, Acta Chimica Slovenica, 55(3), p. 562 (2008). 

Files

Share

How to cite

Statistics