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Russian Journal of Organic Chemistry

, Volume 45, Issue 2, pp 200–205 | Cite as

Benzoid-quinoid tautomerism of azomethines and their structural analogs: LIV. Dibenzo(benzo)-18-crown-6-containing Imines of 5-hydroxy-2,3-tetramethylene- and 5-Hydroxy-2,3-diphenylbenzo[b]furan-4-carbaldehydes

  • A. D. Dubonosov
  • A. V. Tsukanov
  • E. N. Shepelenko
  • Yu. V. Revinskii
  • V. A. Bren’
  • V. I. Minkin
Article

Abstract

Dibenzo(benzo)-18-crown-6-containing N-arylimines of 5-hydroxy-2,3-tetramethylene- and 5-hydroxy-2,3-diphenylbenzo[b]-furan-4-carbaldehydes were synthesized and their spectral luminescence properties were investigated. In solutions of 6-bromo- and 6-nitro-substituted compounds a tautomeric equilibrium exists between the benzoid and quinoid forms. In the course of complexing of crown-ether-imines of 5-hydroxy-6-nitro-2,3-diphenylbenzo[b]furan-4-carbaldehyde and 5-hydroxy-6-nitro-2,3-tetramethylenebenzo[b]furan-4-carbaldehyde with cations of alkali and alkaline earth metals the content of the quinoid form was found to decrease. This phenomenon was accompanied by essential changes in the absorption and fluorescence spectra characteristic of chemosensor systems with an intramolecular charge transfer (ICT).

Keywords

Tetramethylene Intramolecular Charge Transfer Carbaldehyde Spectral Luminescence Property Quinoid Form 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • A. D. Dubonosov
    • 1
  • A. V. Tsukanov
    • 1
  • E. N. Shepelenko
    • 1
  • Yu. V. Revinskii
    • 2
  • V. A. Bren’
    • 2
  • V. I. Minkin
    • 2
  1. 1.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia
  2. 2.Research Institute of Physical and Organic Chemistry at Southern Federal UniversityRostov-on-DonRussia

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