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Synthesis and Optical and Electrochemical Properties of New Push–Pull Chromophores Containing a 1,2-Di(thiophen-2-yl)ethene Fragment

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Abstract

New D–π–A chromophores containing terminal electron-donating triphenylamine and electron-withdrawing 2-(5,5-dimethylcyclohex-2-en-1-ylidene)propanedinitrile (DCM-1) or 2-(6-methyl-4H-pyran-4-ylidene)propanedinitrile (DCM-2) fragments separated by π-conjugated 1,2-di(thiophen-2-yl)ethene spacer have been synthesized. Comparison of the optical and electrochemical properties of the synthesized compounds has shown that the band gap increases in going from DCM-1 to DCM-2 from 1.83 to 2.15 eV. Apart from the narrow band gap, these compounds are characterized by a large Stokes shift (>100 nm) and high absorbance (25000–65000 L·mol–1·cm–1) in the visible region (λ 420–660 nm); therefore, they can be regarded as potential light storage materials and labels and probes for biomedical studies.

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Funding

This study was performed under financial support by the Russian Foundation for Basic Research and by the Government of Perm Krai (project no. 19-43-590014 r-a).

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Authors and Affiliations

  1. Perm State University, 614900, Perm, Russia

    I. V. Chikunova, A. N. Bakiev, E. V. Shklyaeva & G. G. Abashev

  2. Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch, Russian Academy of Sciences, 614013, Perm, Russia

    A. N. Bakiev & G. G. Abashev

Authors
  1. I. V. Chikunova
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  2. A. N. Bakiev
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  3. E. V. Shklyaeva
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  4. G. G. Abashev
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Correspondence to G. G. Abashev.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 7, pp. 744–753 https://doi.org/10.31857/S0514749222070072.

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Chikunova, I.V., Bakiev, A.N., Shklyaeva, E.V. et al. Synthesis and Optical and Electrochemical Properties of New Push–Pull Chromophores Containing a 1,2-Di(thiophen-2-yl)ethene Fragment. Russ J Org Chem 58, 990–996 (2022). https://doi.org/10.1134/S1070428022070077

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