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Russian Journal of Organic Chemistry

, Volume 50, Issue 4, pp 540–543 | Cite as

Photo- and ionochromic properties of aza crown derivatives of enamino 1-benzothiophen-2-ones

  • V. I. Minkin
  • V. A. Bren’
  • A. D. Dubonosov
  • K. S. Tikhomirova
  • E. N. Shepelenko
Article

Abstract

2-(N-Acyl-N-arylaminomethylidene)-1-benzothiophen-3(2H)-ones exhibit photochromic properties due to photoinitiated Z/E isomerization with respect to the exocyclic C=C bond and subsequent fast thermal N→O migration of the acyl group and synanti isomerization of the N-acyl isomer. Introduction of a 15-azacrown-5 substituent into the para position of the aryl group reduces the quantum yield of the N→O rearrangement down to zero. By contrast, under irradiation with a mercury lamp, crown ether complexes with alkaline earth cations are converted almost completely into the O-acyl isomers which, unlike their N-acyl analogs, show no fluorescence. The highest quantum yields for the N→O acyl group migration are observed for the calcium complexes. The obtained compounds constitute a new class of acylotropic molecular switches operating under photoinitiation exclusively in the presence of alkaline earth cations.

Keywords

Crown Ether Electronic Absorption Spectrum Benzoyl Chloride High Quantum Yield Photoinitiation 
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. 2014

Authors and Affiliations

  • V. I. Minkin
    • 1
    • 2
  • V. A. Bren’
    • 1
  • A. D. Dubonosov
    • 2
  • K. S. Tikhomirova
    • 1
  • E. N. Shepelenko
    • 2
  1. 1.Research Institute of Physical and Organic ChemistrySouthern State UniversityRostov-on-DonRussia
  2. 2.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia

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