Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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The Novel Functional Chromophores Based on Squarylium Dyes

  • Park, Soo-Youl (Department of Applied Chemistry, Dye, Dyeing and Finishing Center, Korea Research Institute of Chemical Technology) ;
  • Jun, Kun (Department of Applied Chemistry, Dye, Dyeing and Finishing Center, Korea Research Institute of Chemical Technology) ;
  • Oh, Sea-Wha (Department of Applied Chemistry, Dye, Dyeing and Finishing Center, Korea Research Institute of Chemical Technology)
  • Published : 2005.03.20
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Abstract

Squarylium or squaraine dyes are derived from 1,2-dihydroxycyclobuten-3,4-dione, otherwise known as squaric acids. They are two principal types: the 1,2-bisdonorsubstituted derivatives, and the 1,3-bisdonorsubstituted derivatives. The former are essentially merocyanines and have no distinctive properties, whereas the latter represent a unique type of chromophore, which is neither a merocyanines nor cyanine and has exceptional light absorption characteristics. They also have many functional applications based on their special properties. Thus it was the objective of this research project to synthesize a range of 1,3-squarylium dyes of widely differing structural types, and to investigate their light absorption and fluorescence properties in general, and the color change properties of appropriate examples in particular. Also in this study, the various pHinduced colour change processes were examined.

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References

  1. Schmidt, A. H.; Ried, W. Synthesis 1978, 869
  2. Dirk, C. W.; Herndon, W. C.; Cervantes-Lee, F.; Martinez, H. S.; Kalamegham, P.; Tag, A.; Campos, G.; Velez, M.; Zyss, J.; Ledoux, I.; Cheng, L. T. J. Am. Chem. Soc. 1995, 117, 2214 https://doi.org/10.1021/ja00113a011
  3. Reans, F. J. Chem. Soc. 1996, 92(19), 3611
  4. Matsuoka, M.; Yasui, S.; Kitao, T. Dyes and Pigments 1988, 10, 13 https://doi.org/10.1016/0143-7208(89)85036-3
  5. Junek, H.; Hermetter, A.; Colbrie, H. F.; Aigner, H. Tetrahedron Letters 1973, 2993
  6. Vogel, A. I. Textbook of Practical Organic Chemistry, 4th Ed; Longman: London and New York., 1978; p 677

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