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


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.


Crown Ether Electronic Absorption Spectrum Benzoyl Chloride High Quantum Yield Photoinitiation 
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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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