The Synthesis of New Leuco Squarylium Dyes

  • Park, Soo-Youl (Bio Fine Chemical Research Center, Korea Research Institute of Chemical Technology) ;
  • Jun, Kun (Bio Fine Chemical Research Center, Korea Research Institute of Chemical Technology) ;
  • Shin, Seung-Rim (Bio Fine Chemical Research Center, Korea Research Institute of Chemical Technology) ;
  • Shin, Jong-Il (Bio Fine Chemical Research Center, Korea Research Institute of Chemical Technology)
  • Published : 2007.10.27

Abstract

It is well known that certain classes of dye are reducible to stable colorless leuco compounds, which can be oxidized in air back to the colored species. We now reported that bis(4-dialkylaminophenyl)squaraine dyes are readily reduced in solution by borohydride to give alkali soluble leuco compound, which exists in the 3-hydroxy 2,4-bis(4-dialkylaminophenyl)cyclobuten-one. New alkylamine leuco compounds were synthesized by the reaction of leuco chloro-squaraine with alkylamine derivatives. The leuco compounds are easily isolated and can be air oxidized back to the squaraine dyes. These dyes have many technical application. e.g. in xerography, solar cell, optical recording material, redox indicators, and enzyme assays.

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References

  1. V. Y. Merrit, and H. J. Hovel, Organic Solar Cells of Hydroxy Squarylium, Appl Phys Lett., 29, 414(1976) https://doi.org/10.1063/1.89101
  2. D. L. Morel, E. L. Stogryn, A. G.. Ghosh, T. Feng, P. E. Purwin, and R. F. Show, Organic Photovoltaic Cells: Correlations between cell performance and molecular structure, J. Phys Chem., 88, 923(1984) https://doi.org/10.1021/j150649a019
  3. A. C. Tam, Optoacoustic determination of photocarrier generation efficiencies of dye films, Appl Phys Lett., 37, 978(1980) https://doi.org/10.1063/1.91725
  4. R. O. Loufty, A. M. Hor, C. K. Hsiao, G. Baranyi, and P. Kazmeier, Organic Photoconductive Materials, Pure Appl Chem., 60, 1047(1988) https://doi.org/10.1351/pac198860071047
  5. K. Y. Law, Organic Photoconductive Materials: Recent Trends and Developments, Chem Rev., 93, 449(1993) https://doi.org/10.1021/cr00017a020
  6. M. Emmelius, G.. Pawlowski and H. W. Vollmann, Materialien für die optische datenspeicherung, Angew Chem., 101, 1475(1989) https://doi.org/10.1002/ange.19891011104
  7. M. Matsuoka, Infrared absorbing dyes., New York; Plenum, 1990
  8. S. Daehne, V. Resch-Genber, and O. S. Wolfbeis, Near-infrared dyes for high technology application, London; Kluwer Academic Publishers, 1997
  9. J. Fabian and H. Hartmann, 'Light Absorption of Organic Colorants', Springer Verlag, Berlin, P.124, 1980
  10. J. Formanek, Uber den einfluss verschiedener substituenten auf farbe und absorptionsspektrum des indigo, thioindigo und indirubin, Angew. Chem., 41, 1133(1928) https://doi.org/10.1002/ange.19280414102
  11. A. P. Piechowski, G. R. Bird, D. L. Morel, and E. L. Stogryn, Desirable Properties of Photovoltaic Dyes, J. Phys, Chem., 88, 934-950 (1984) https://doi.org/10.1021/j150649a020
  12. S. Das, K. G. Thomas, K. J. Thomas, M. V. Georage, I. Bedja, and P. V. Kamat, Crown ether derivative of squaraine: New Infrared Absorbing Redox Active Fluoroionophores for Alkali Metal Recognition, Anal. Proc., 32, 213-215(1995) https://doi.org/10.1039/ai9953200213
  13. P. V. Kamat, S. Das, K. G. Thomas, and V. J. Manapuratha, Photochemistry of Squaraine Dyes: Excited singlet, triplet and redox states of squaraine, Phys, Chem., 96, 195-199 (1992) https://doi.org/10.1021/j100180a038