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New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety

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Abstract

New D-π-A-type chromophores that simultaneously incorporate N,N-dimethylaminophenyl moiety as the terminal electron-donating group and either (5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile (DCM-1) or (6-methyl-4H-pyran-4-ylidene)malononitrile (DCM-2) unit as the terminal electron-withdrawing group were synthesized. Vinylene moiety and azo group served as the π-spacer. A comparative analysis of optical and electrochemical properties of the synthesized chromophores revealed that the replacement of the DCM-1 unit with the DCM-2 moiety led to chromophore band gap broadening and a decrease in the molar extinction coefficient value; while the replacement of the DCM-1 unit with the DCM-2 one in the chromophores bearing the vinylene π-spacers led to a sharp increase in the fluorescence quantum yield.

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Funding

This work was financially supported by the Russian Foundation for Basic Research and Perm Territory (Project No. 19-43-590014).

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Authors and Affiliations

  1. Institute of Technical Chemistry Ural Branch Russian Academy of Sciences - Branch of the Perm Federal Research Center Ural Branch Russian Academy of Sciences, 3 ul. Akad. Koroleva, 614013, Perm, Russian Federation

    D. G. Slobodinyuk & G. G. Abashev

  2. Perm State University, 15 ul. Bukireva, 614990, Perm, Russian Federation

    A. N. Vasyanin, I. V. Lunegov, E. V. Sklyaeva & G. G. Abashev

Authors
  1. D. G. Slobodinyuk
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  2. A. N. Vasyanin
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  3. I. V. Lunegov
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  4. E. V. Sklyaeva
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  5. G. G. Abashev
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Corresponding authors

Correspondence to D. G. Slobodinyuk or G. G. Abashev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 341–349, February, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Slobodinyuk, D.G., Vasyanin, A.N., Lunegov, I.V. et al. New D-π-A chromophores incorporating (5,5-dimethylcyclohex-2-en-1-ylidene)- or (6-methyl-4H-pyran-4-ylidene)-malononitrile moiety. Russ Chem Bull 71, 341–349 (2022). https://doi.org/10.1007/s11172-022-3417-2

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  • DOI: https://doi.org/10.1007/s11172-022-3417-2

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