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New chromophores based on 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile

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Abstract

New derivatives of 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile were synthesized using the Knoevenagel reaction of 2-(4-methyl-chromen-2-ylidene)malononitrile and 2-(2-methylchromen-4-ylidene)malononitrile, respectively, with the participation of [1-(2-n-butoxyethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)]-carbaldehyde. First hyperpolarizability (β) was calculated for the obtained compounds using the M05-2X functional and 6-31+G (d) basis. Optical properties and solvatochromism in solvents of different polarity (toluene, 1,4-dioxane, chlorobenzene, dichloromethane, DMF, and ethanol) were also investigated.

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Authors and Affiliations

  1. Central Research Technological Institute Technomash, 4 ul. Ivana Franko, 121108, Moscow, Russian Federation

    K. S. Levchenko, K. A. Chudov, D. Yu. Demin, G. E. Adamov, E. V. Zinoviev & P. S. Shmelin

  2. Chemistry Department, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    K. A. Lyssenko

  3. G. V. Plechanov Russian Economical University, 36 Stremyanniy per., 117997, Moscow, Russian Federation

    K. A. Lyssenko

  4. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Build. 4, 31 Leninsky prosp., 119071, Moscow, Russian Federation

    A. V. Shokurov

  5. MIREA – Russian Technological University, 78 prosp. Vernadskogo, 119454, Moscow, Russian Federation

    E. P. Grebennikov

Authors
  1. K. S. Levchenko
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  2. K. A. Chudov
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  3. D. Yu. Demin
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  4. G. E. Adamov
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  5. E. V. Zinoviev
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  6. K. A. Lyssenko
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  7. A. V. Shokurov
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  8. P. S. Shmelin
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  9. E. P. Grebennikov
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Correspondence to K. S. Levchenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1883–1888, October, 2019.

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Levchenko, K.S., Chudov, K.A., Demin, D.Y. et al. New chromophores based on 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile. Russ Chem Bull 68, 1883–1888 (2019). https://doi.org/10.1007/s11172-019-2641-x

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  • DOI: https://doi.org/10.1007/s11172-019-2641-x

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