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Photochromic and thermochromic spiranes 33. Synthesis of a new indolinonaphthoxazino- bisspiropyran and investigation of its photochromic characteristics

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Chemistry of Heterocyclic Compounds Aims and scope

A new unsymmetrical bisspiropyran was synthesized on the basis of 2,4-dihydroxyisophthalic aldehyde with naphthoxazinone and indoline fragments in the structure. The structure of the obtained compound was proved by the data from 1H NMR and IR spectroscopy and X-ray crystallographic analysis. The photochromic characteristics of the obtained compound were investigated. It was established by means of the data from B3LYP/6-31G** quantum-chemical calculations that irradiation of a solution of the obtained biphotochrome with unfiltered light leads to opening of both pyran fragments. This is the first corroborated example of the twofold cleavage of Cspiro–O bonds for compounds of this class.

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, 344090, Russia

    E. L. Mukhanov, I. V. Dorogan, B. S. Lukyanov, V. I. Minkin & O. N. Ryashchin

  2. Southern Scientific Center, Russian Academy of Sciences, Rostov-on-Don, 344090, Russia

    Yu. S. Alekseenko & S. O. Bezuglyi

  3. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, 142432, Moscow Region, Russia

    V. V. Tkachev, S. M. Aldoshin & A. N. Utenyshev

Authors
  1. E. L. Mukhanov
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  2. Yu. S. Alekseenko
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  3. I. V. Dorogan
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  4. V. V. Tkachev
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  5. B. S. Lukyanov
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  6. S. M. Aldoshin
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  7. S. O. Bezuglyi
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  8. V. I. Minkin
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  9. A. N. Utenyshev
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  10. O. N. Ryashchin
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Corresponding author

Correspondence to B. S. Lukyanov.

Additional information

Dedicated to Professor M. A. Yurovskaya on her birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 357-372, March, 2010.

For Communication 32 see [1].

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Mukhanov, E.L., Alekseenko, Y.S., Dorogan, I.V. et al. Photochromic and thermochromic spiranes 33. Synthesis of a new indolinonaphthoxazino- bisspiropyran and investigation of its photochromic characteristics. Chem Heterocycl Comp 46, 279–290 (2010). https://doi.org/10.1007/s10593-010-0503-4

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  • DOI: https://doi.org/10.1007/s10593-010-0503-4

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