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Russian Journal of Organic Chemistry

, Volume 53, Issue 11, pp 1726–1737 | Cite as

Synthesis, structure, spectral properties, and electrochemistry of bis(crown ether) containing 1,3-distyrylbenzenes

  • V. N. Nuriev
  • O. V. Fedorov
  • A. A. Moiseeva
  • A. Ya. Freidzon
  • N. A. Kurchavov
  • A. I. Vedernikov
  • A. V. Medved’ko
  • E. S. Pod’yacheva
  • S. Z. Vatsadze
  • S. P. Gromov
Article
  • 31 Downloads

Abstract

The reaction of tetraethyl [1,3-phenylenedi(methylene)]bis(phosphonate) with formyl derivatives of benzocrown-ethers or formyl derivatives of o-dimethoxybenzene lead to high yield formation of the respectful bis(crown ether) containing 1,3-distyrylbenzenes or tetramethoxy-substituted 1,3-distyrenebenzenes. NMR spectra and quantum-chemical calculations showed the prevalence of unsymmetrical syn/anti,(syn,anti),syn/anti-conformations in 1,3-distyrylbenzenes. 1,3-Distyrylbenzenes absorb in shorter wavelength spectral region and have a weaker fluorescence than 1,4-distyrylbenzenes. The difficulty in the electrochemical reduction of 1,3-distyrylbenzenes comparing with 1,4-distyrylbenzenes is due to a less effective conjugation system in the metaderivatives.

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Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • V. N. Nuriev
    • 1
  • O. V. Fedorov
    • 2
  • A. A. Moiseeva
    • 1
  • A. Ya. Freidzon
    • 3
  • N. A. Kurchavov
    • 3
  • A. I. Vedernikov
    • 3
  • A. V. Medved’ko
    • 1
  • E. S. Pod’yacheva
    • 1
  • S. Z. Vatsadze
    • 1
  • S. P. Gromov
    • 1
    • 3
  1. 1.Lomonosov Moscow State UniversityMoscowRussia
  2. 2.Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia
  3. 3.Photochemistry Center of the Russian Academy of SciencesMoscowRussia

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