Enhancement of Fluorescent Properties and Electrochemical Reduction of Coumarin Derivatives

Coumarin 유도체들의 전기화학적 환원과 형광성의 증강

  • Chun, Hyun Ja (Department of Chemistry, College of Natural Science and Institute of Basic Natural Science, Wonkwang University) ;
  • Kim, Sung Hyun (Department of Chemistry, College of Natural Science and Institute of Basic Natural Science, Wonkwang University) ;
  • Jung, Eun Joo (Department of Chemistry, College of Natural Science and Institute of Basic Natural Science, Wonkwang University) ;
  • Lee, Hye Suk (Drug Metabolism and Bioanalysis Laboratory, College of Pharmacy and Phytofermentation Research Center, Wonkwang University) ;
  • Kim, Il Kwang (Department of Chemistry, College of Natural Science and Institute of Basic Natural Science, Wonkwang University)
  • 천현자 (원광대학교 자연과학대학 화학과) ;
  • 김성현 (원광대학교 자연과학대학 화학과) ;
  • 정은주 (원광대학교 자연과학대학 화학과) ;
  • 이혜숙 (원광대학교 약학대학 약학과) ;
  • 김일광 (원광대학교 자연과학대학 화학과)
  • Received : 2005.01.04
  • Accepted : 2005.01.31
  • Published : 2005.02.25

Abstract

Studies on the electrochemical reduction of 7-acetoxy-4-bromomethyl-coumarin (ABMC), 7-acetoxymethyl coumarin (AMC), and coumarin in 0.1 M tetraethyl ammonium perchlorate acetonitrile solution were carried out with direct current, differential pulse polarography, cyclic voltammetry, and controlled potential coulometry. The electrochemical reduction of ABMC was proceeded through three irreversible steps coupled with the chemical reactions. The solution color was changed to yellow when the carbonyl group was reduced during second step and the color change was independent with bromo group of ABMC. Fluorescent intensity was highest when the electrochemical reduction was controlled at near the overpotential of supporting electrolyte (-2.3 volts).

Keywords

References

  1. L. Brace, Amer. J. Medical Technology, 49, 457 (1983)
  2. B. G. Lake, Archieves of Toxicology, 7, 16(1984)
  3. S. H. Yuen, Analyst, 103, 842(1978) https://doi.org/10.1039/an9780300842
  4. Colaborative International Perticides Analytical Council(CIPAC), Edited by G. R. Raw, printed in Great Britain, by W. Heffer & Sons Ltd, Cambridge, Vol. 1, p.696-702(1970)
  5. M. H. Salaman, J. Cancer, 9, 177(1967)
  6. E. C. Hogan, Fed. Cosmet. Tosicol., 5, 141(1967) https://doi.org/10.1016/S0015-6264(67)82961-4
  7. A. J. Harle and L. E. Lyons, J. Chem. Soc., 1575 (1950) https://doi.org/10.1039/jr9500001575
  8. O. Capka, Coll. Czech. Chem. Commun., 15, 965 (1950) https://doi.org/10.1135/cccc19500965
  9. P. Zuman, Chem. Listy, 48, 94(1954)
  10. P. Zuman, 'Organic Polarographic Analysis,' Pergamon Press, New York, 251(1964)
  11. P. Zuman, 'Substituent Effects in Organic Polarography,' Plenum Press, New York, 165 (1967)
  12. R. N. Gourley, J. Grimshaw, and P. G. Miller, J. Chem. Soc.(C), 2318(1970) https://doi.org/10.1039/j39700002318
  13. B. O. Reddy, A. V. Reddy, K. M. Raju, A. K. Rao, J. Electrochem. Soc. India, 35, 319(1989)
  14. L. K. Partridge, A. C. Tansley, and A. S. Porter, Electrochemical Acta, 11, 517(1966) https://doi.org/10.1016/0013-4686(66)80028-2
  15. A. M. Bond, F. G. Thomas, Langmuir, 4, 341 (1988) https://doi.org/10.1021/la00080a016
  16. J. M. P. Carrazon, A. G. Vergara, A. J. R. Garcia, and L. M. P. Diez, Anal. Chim. Acta, 216, 231 (1989) https://doi.org/10.1016/S0003-2670(00)82010-3
  17. E. Dempsey, C. O'Sullivan, M. R. Smyth, D. Egan, R. O'kennedy, and J. Wang, J. Pharm. Biomed. Anal., 11, 443(1993) https://doi.org/10.1016/0731-7085(93)80155-T
  18. E. Dempsey, C. O'Sullivan, M. R. Smyth, D. Egan, R. O'kennedy, and J. Wang, Analyst, 118, 411 (1993) https://doi.org/10.1039/an9931800411
  19. C. R. Moylan, J. Phys. Chem., 98, 13513 (1994) https://doi.org/10.1021/j100102a014
  20. S. M. Park, A. J. Bard, J. Electroanal. Chem., 77, 137(1977) https://doi.org/10.1016/S0022-0728(77)80467-1
  21. P. Paniez, G. Amblard, Microelectron. Eng., 5, 321 (1986) https://doi.org/10.1016/0167-9317(86)90060-2
  22. F. G. Zhang, C. L. Yu, J. Appl. Phys., 62, 49 (1987) https://doi.org/10.1063/1.339158
  23. G. Jones II, M. A. Rahman, J. Phys. Chem., 98, 13028(1994) https://doi.org/10.1021/j100100a035
  24. D. D. Perrin and W. L. F. Armarego, 'Purification of Laboratory Chemicals,' 3rd. Ed., Pergamon Pressm Oxford, 69(1988)
  25. P. Zuman, 'The Elucidation of Organic Electrode Processess,' Acdemic Press, New York, p.7-10, p.155, p.170, p.223(1969)