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Synthesis, structures, and photochromic properties of 3-[(E)-alk-1-enyl]-4-(1-alkyl-5-methoxy-2-methyl-1H-indol-3-yl)furan-2,5-diones

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Abstract

New hetarylethenes, viz., 3-[(E)-alk-1-enyl]-4-(1-alkyl-5-methoxy-2-methyl-1H-indol-3-yl)furan-2,5-diones, exhibiting photochromic properties in solution were synthesized. The molecular and crystal structure of 3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-4-[(E)-prop-1-enyl]furan-2,5-dione was determined by X-ray diffraction. The initial and photoinduced forms of hetarylethenes are characterized by thermal stability. The open-ring isomers of furandiones exhibit fluorescence with quantum yields of up to 0.1.

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Authors and Affiliations

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

    N. I. Makarova, P. V. Levchenko, A. V. Metelitsa, L. L. Popova, V. A. Bren’ & V. I. Minkin

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. V. Tkachev & S. M. Aldoshin

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

    E. N. Shepelenko, V. P. Rybalkin & V. I. Minkin

Authors
  1. N. I. Makarova
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  2. P. V. Levchenko
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  3. V. V. Tkachev
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  4. E. N. Shepelenko
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  5. A. V. Metelitsa
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  6. V. P. Rybalkin
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  7. L. L. Popova
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  8. V. A. Bren’
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  9. S. M. Aldoshin
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  10. V. I. Minkin
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Corresponding author

Correspondence to L. L. Popova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1065–1070, June, 2011.

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Makarova, N.I., Levchenko, P.V., Tkachev, V.V. et al. Synthesis, structures, and photochromic properties of 3-[(E)-alk-1-enyl]-4-(1-alkyl-5-methoxy-2-methyl-1H-indol-3-yl)furan-2,5-diones. Russ Chem Bull 60, 1090–1095 (2011). https://doi.org/10.1007/s11172-011-0172-1

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  • DOI: https://doi.org/10.1007/s11172-011-0172-1

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