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Synthesis and nonlinear optical properties of donor-acceptor dyes based on triphenylpyrazolines as a donor block and dicyanoisophorone as acceptor

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Abstract

A series of donor-acceptor dyes based on polyfluoro-substituted triarylpyrazolines (as a donor block) and a dicyanoisophorone group (as an acceptor) were synthesized using the Knoevenagel condensation. The dyes have an absorption in the region of 509–514 nm and intense luminescence at 648–663 nm in chloroform with a large Stokes shift (up to 4410 cm–1). Based on the synthesized dyes, chromophore–polymer (guest–host) films were obtained in a polycarbonate matrix with a chromophore content up to 27 wt.%. Poling of chromophore–polymer films was carried out in an electric field of a corona discharge and the coefficient of nonlinear optical response d33 was measured by the second-harmonic generation method of the fundamental frequency of a Nd-YAG laser (1064 nm). The obtained films have a high initial thermal stability and a nonlinear optical response up to 80 pm V–1, which persists up to 115 °С.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrenteva, 630090, Novosibirsk, Russian Federation

    V. V. Shelkovnikov, I. Yu. Kargapolova, N. A. Orlova, S. V. Korotaev, A. E. Simanchuk & S. L. Mikerin

  2. Novosibirsk State Technical University, 20 prosp. Marksa, 630073, Novosibirsk, Russian Federation

    V. V. Shelkovnikov

  3. Institute of Automation and Electrometry, Siberian Branch of the Russian Academy of Sciences, 1 prosp. Akad. Koptyuga, 630090, Novosibirsk, Russian Federation

    A. E. Simanchuk & S. L. Mikerin

Authors
  1. V. V. Shelkovnikov
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  2. I. Yu. Kargapolova
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  3. N. A. Orlova
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  4. S. V. Korotaev
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  5. A. E. Simanchuk
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  6. S. L. Mikerin
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Corresponding author

Correspondence to V. V. Shelkovnikov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0092–0098, January, 2019.

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Shelkovnikov, V.V., Kargapolova, I.Y., Orlova, N.A. et al. Synthesis and nonlinear optical properties of donor-acceptor dyes based on triphenylpyrazolines as a donor block and dicyanoisophorone as acceptor. Russ Chem Bull 68, 92–98 (2019). https://doi.org/10.1007/s11172-019-2421-7

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  • DOI: https://doi.org/10.1007/s11172-019-2421-7

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