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

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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 syn→anti 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.

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References

  1. Bouas-Laurent, H. and Dürr, H., Pure Appl. Chem., 2001, vol. 73, p. 639.

    Article  CAS  Google Scholar 

  2. Photochromism: Molecules and Systems, Dürr, H. and Bouas-Laurent, H., Amsterdam: Elsevier, 2003.

    Google Scholar 

  3. Organic Photochromic and Thermochromic Compounds, Crano, J.C. and Guglielmetti, R., New York: Kluwer Academic/Plenum, 1999, vols. 1, 2.

  4. Minkin, V.I., Russ Chem. Rev., 2013, vol. 82, p. 1.

    Article  Google Scholar 

  5. Paramonov, S.V., Lokshin, V., and Fedorova, O.A., J. Photochem. Photobiol. C: Photochem. Rev., 2011, vol. 12, p. 209.

    Article  CAS  Google Scholar 

  6. Minkin, V.I., Bren’, V.A., Dubonosov, A.D., and Tsukanov, A.V., Chem. Heterocycl. Compd., 2012, vol. 48, no. 1, p. 107.

    Article  CAS  Google Scholar 

  7. Bren, V.A., Dubonosov, A.D., Popova, L.L, Rybalkin, V.P., Sadekov, I.D., Shepelenko, E.N., and Tsukanov, A.V., Arkivoc, 2005, part (vii), p. 60.

    Google Scholar 

  8. Rybalkin, V.P., Vorob’ëva, Ya.Yu., Borodkin, G.S., Dubonosov, A.D., Tsukanov, A.V., Tkachev, V.V., Aldoshin, S.M., Bren’, V.A., and Minkin, V.I., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 2783.

    Article  CAS  Google Scholar 

  9. Dubonosov, A.D., Minkin, V.I., Bren, V.A., Popova, L.L., Rybalkin, V.P., Shepelenko, E.N., Tkalina, N.N., and Tsukanov, A.V., Arkivoc, 2003, part (xiii), p. 12.

    Google Scholar 

  10. Bren, V.A., Dubonosov, A.D., Minkin, V.I., Gribanova, T.N., Rybalkin, V.P., Shepelenko, E.N., Tsukanov, A.V., and Borisenko, R.N., Mol. Cryst. Liq. Cryst., 2005, vol. 431, p. 417.

    Article  CAS  Google Scholar 

  11. Bren, V.A., Dubonosov, A.D., Minkin, V.I., Tsukanov, A.V., Gribanova, T.N., Shepelenko, E.N., Revinsky, Y.V., and Rybalkin, V.P., J. Phys. Org. Chem., 2007, vol. 20, p. 917.

    Article  CAS  Google Scholar 

  12. Tsukanov, A.V., Dubonosov, A.D., Bren, V.A., and Minkin, V.I., Chem. Heterocycl. Compd., 2008, vol. 44, no. 8, p. 899.

    Article  CAS  Google Scholar 

  13. Aldoshin, S.M., Dyachenko, O.A., Atovmyan, L.O., Minkin, V.I., Bren, V.A., and Paluy, G.D., Z. Kristallogr., 1982, vol. 159, p. 143.

    CAS  Google Scholar 

  14. Dubonosov, A.D., Rybalkin, V.P., Popova, L.L., Tsukanov, A.V., Revinsky, Yu.V., Bren, V.A., and Minkin, V.I., Int. J. Photoenergy, 2009, vol. 2009, article ID 694196.

  15. Tsivadze, A.Yu., Varnek, A.A., and Khutorskii, V.E., Koordinatsionnye soedineniya metallov s kraun-ligandami (Metal Coordination Compounds with Crown Ligands), Moscow: Nauka, 1991.

    Google Scholar 

  16. Hatchard, C.G. and Parker, C.A., Proc. R. Soc. A, 1956, vol. 235, p. 518.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern State University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    V. I. Minkin, V. A. Bren’ & K. S. Tikhomirova

  2. Southern Scientific Center, Russian Academy of Sciences, pr. Chekhova 41, Rostov-on-Don, 344006, Russia

    V. I. Minkin, A. D. Dubonosov & E. N. Shepelenko

Authors
  1. V. I. Minkin
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  2. V. A. Bren’
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  3. A. D. Dubonosov
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  4. K. S. Tikhomirova
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  5. E. N. Shepelenko
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Correspondence to V. I. Minkin.

Additional information

Original Russian Text © V.I. Minkin, V.A. Bren’, A.D. Dubonosov, K.S. Tikhomirova, E.N. Shepelenko, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 4, pp. 551–554.

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Minkin, V.I., Bren’, V.A., Dubonosov, A.D. et al. Photo- and ionochromic properties of aza crown derivatives of enamino 1-benzothiophen-2-ones. Russ J Org Chem 50, 540–543 (2014). https://doi.org/10.1134/S1070428014040162

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  • DOI: https://doi.org/10.1134/S1070428014040162

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