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Novel asymmetric dihetarylethenes derived from N-isopropylindole and thiophene: synthesis and photochromic properties

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Abstract

Novel asymmetric dihetarylethenes, viz., 3-(1-isopropyl-5-methoxy-2-methyl-1H-indol-3-yl)-4-(3-thienyl)furan-2,5-dione and 1-alkyl/aryl-3-(1-isopropyl-5-methoxy-2-methyl-1H-indol-3-yl)-4-(3-thienyl)-1H-pyrrole-2,5-diones, were obtained. These dihetarylethenes exhibit photochromism in solutions. Replacement of the N-methyl group in the indole fragment by the N-isopropyl group imparts photochromic properties to the resulting furan-2,5-dione derivative. The open forms of (N-isopropylindol-3-yl)pyrrole-2,5-diones are characterized by lower quantum yields of fluorescence, and their cyclic forms are thermally more stable.

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    N. I. Makarova, A. V. Metelitsa, V. A. Bren’ & V. I. Minkin

  2. Southern Scientific Center of the Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov-on-Don, Russian Federation

    E. N. Shepelenko & V. I. Minkin

Authors
  1. N. I. Makarova
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  2. E. N. Shepelenko
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  3. A. V. Metelitsa
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  4. V. A. Bren’
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  5. V. I. Minkin
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Correspondence to N. I. Makarova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2424–2429, Novemer, 2013.

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Makarova, N.I., Shepelenko, E.N., Metelitsa, A.V. et al. Novel asymmetric dihetarylethenes derived from N-isopropylindole and thiophene: synthesis and photochromic properties. Russ Chem Bull 62, 2424–2429 (2013). https://doi.org/10.1007/s11172-013-0350-4

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  • DOI: https://doi.org/10.1007/s11172-013-0350-4

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