Color Change Redox Behavior of the 1,3-Squaraine Dyes

  • Jun, Kun (Korea Research Institute of Chemical Technology, New Chemistry Research Division, Colorant Chemistry Research Team) ;
  • Shin, Seung-Rim (Korea Research Institute of Chemical Technology, New Chemistry Research Division, Colorant Chemistry Research Team) ;
  • Shin, Jong-Il (Korea Research Institute of Chemical Technology, New Chemistry Research Division, Colorant Chemistry Research Team) ;
  • Park, Soo-Youl (Korea Research Institute of Chemical Technology, New Chemistry Research Division, Colorant Chemistry Research Team)
  • Published : 2006.10.27

Abstract

The 1,3-bis(4-aminoaryl)squaraines showed color, change behavior, they were found to undergo reduction with sodium borohydride in solution to give colorless leuco compounds, which oxidized readily in air back to the colored squaraine dye. We have shown that initial observations indicated that the derivatives synthesized gave new donor-acceptor chromophores. It is also interesting to note than the oxidation of the leuco squaraines did initially produce a species absorbing about 630-680 wavelengths. The 1,3-squaraines have found many uses as near-infrared absorbers, laser dyes and photoconductive materials. Furthermore their color-change redox behavior has potential in the area of peroxidase-based bioassaysas oxidation sensitive indicator systems were investigated.

Keywords

References

  1. K. Y. Law, J. S. Facci, F. C. Bailey, and J. F. Yanus. J. Imaging Science, 34, 31(1990)
  2. S. Das, K. G. Thomas, K. J. Thomas, M. V. George, I. Bedja, and P. V. Kamat. Anal. Proc., 32, 213(1995)
  3. N. Takeda, M. E. Stawasz, and B. A. Parkinson. Electrochemical Oxidation and Ex-situ STM Observations of Bis(4-dimethylamino-2-dihy-droxyphenyl)squaraine Dye Layer on HOPG Electrodes, J. Electroanal. Chem., 19, 498(2001)
  4. M. R.. Detty and B. Henne, Squarylium Dyes Based on 2,6-Di-tert-butylselenopyrylium or Tell-uropylium Nuclei, Heterocycles, 35, 1149(1993) https://doi.org/10.3987/COM-92-S(T)115
  5. L. Tong, B-X. Peng, L-Z. Fan, Y-F. Li, F-L. Bai, Z-H. Peng, and H. Geise, Solution Electrochemistry of Indolenium Squarylium Cyanine Dyes, Dyes and Pigments, 42, 113(1999) https://doi.org/10.1016/S0143-7208(98)00078-3
  6. K. Y. Law, J. S. Facci, F. C. Bailey, and J. F. Yanus. J. Imaging Science, 34, 31(1990)
  7. B. Patrick, M. V. George, P. V. Kamat, S. Das, and K. G. Thomas. Photochemistry of Squaraine Dyes, J. Chem. Soc. Faraday Trans., 88, 671(1992) https://doi.org/10.1039/ft9928800671
  8. P. V. Kamat, S. Das, K. G. Thomasand and M. V. George. Excited Singlet, Triplet, and Redox State of Bis[4-(dimethylamino)phenyl]squaraine, J. Phys. Chem., 96, 195(1992) https://doi.org/10.1021/j100180a038
  9. G. Sauve, P. V. Kamat, K. G. Thomas, K. J. Thomas, S. Das, M. V. George. Excited Triplet State and Redox Properties of Crown Ether Squaraines, J. Phys. Chem., 100, 2117(1996) https://doi.org/10.1021/jp9520815
  10. H. Junek, A. Hermetter, H. Fischer Colbrie and H. Aigner, Tetrahedron Letters, 2993, 1973
  11. A. H. Schmidt, W. Ried, Synthesis, 869, 1978