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Schiff base compounds derived from (R)-3-phenyl-2-phthalimidopropionic acid: photochromism, solvatochromism, and fluorescence

Abstract

The photochromic behaviors of four Schiff bases derived from (R)-3-phenyl-2-phthalimidopropionic acid were studied to reveal the substituent effect on the photosensitivity. Upon ultraviolet light radiation, all of compounds 14 exhibit photochromic behavior in solution through intramolecular hydrogen atom transfer. In solid state, only compound 2 is photochromic, which may be due to the presence of meta-site methoxyl. In solution, the photochromic behavior of compound 3 is remarkable than the other compounds, which may be ascribed to the presence of para-site hydroxyl. Only compound 4 exhibits solvatochromism, which may be ascribed to the large dissociation tendency of the naphthol hydroxyl. The influences of acidity on the UV–Vis absorption spectra of the title compounds were also studied.

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Acknowledgments

This work was supported by the Natural Science Foundation of Fujian, PR China (2008J0237)

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Correspondence to Qinghua Wang.

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Wang, Q., Qiu, W., Wu, J. et al. Schiff base compounds derived from (R)-3-phenyl-2-phthalimidopropionic acid: photochromism, solvatochromism, and fluorescence. Struct Chem 24, 295–301 (2013). https://doi.org/10.1007/s11224-012-0079-y

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Keywords

  • Photochromism
  • Solvatochromism
  • Fluorescence
  • Schiff base
  • Tautomerism
  • Synthesis