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New thermally stable photochromic di(het)arylethenes of the cyclopentenone series

Abstract

Oxidation of 2,3-diarylcyclopent-2-en-1-ones with m-chloroperoxybenzoic acid gave new thermally stable sulfone derivatives of photochromic diarylethenes. The spectral properties of the compounds obtained (the wavelengths of the maxima of the absorption bands of their initial and cyclic forms, the quantum yields of photocyclization and photobleaching reactions) as well as their thermal stability and fatigue resistance were examined. The relationship between the structures of the synthesized compounds and their photochromic properties was determined. The energy differences between the ground-state molecules of the starting and photoinduced isomers of 2,3-diarylcyclopent-2-en-1-ones were calculated by the DFT/B3LYP1 method with the 6-31G(d) basis set. The calculated energy differences can be used to predict and explain such spectral characteristics of photochromic diarylethenes as the thermal stability of photoinduced isomers and the quantum yields of cycloreversion reactions.

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Correspondence to V. Z. Shirinian.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1753–1759, September, 2012.

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Lonshakov, D.V., Shirinian, V.Z., Lvov, A.G. et al. New thermally stable photochromic di(het)arylethenes of the cyclopentenone series. Russ Chem Bull 61, 1769–1775 (2012). https://doi.org/10.1007/s11172-012-0243-y

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  • DOI: https://doi.org/10.1007/s11172-012-0243-y

Key words

  • diarylethenes
  • photochromes
  • quantum yield
  • thermal stability
  • cyclopentenones
  • sulfones
  • photoinduced isomers
  • density functional theory (DFT)
  • B3LYP1 functional