A facile and convenient synthesis and photovoltaic characterization of novel thieno[2,3-b]indole dyes for dye-sensitized solar cells

Roman A. Irgashev, Arseny A. Karmatsky, Sergey A. Kozyukhin, Vladimir K. Ivanov, Alexey Sadovnikov, Vladimir V. Kozik, Vitaly A. Grinberg, Viktor V. Emets, Gennady L. Rusinov, Valery N. Charushin

    Research output: Contribution to journalArticle

    26 Citations (Scopus)

    Abstract

    Two novel dyes IK-1,2 bearing the 8-alkyl-8H-thieno[2,3-b]indole unit as an electron-donating part of the push-pull system have been designed and prepared, as promising sensitizers for solar cells. The key steps of the synthesis involve the crotonic condensation of 1-alkylisatins with 2-acetylthiophene, followed by reduction of the C=C double bond and further cyclization through the Paal-Knorr reaction with the Lawesson reagent, thus leading to the formation of 2-(thien-2-yl) substituted thieno[2,3-b] indole derivatives. The optical and electrochemical properties of these dyes have been investigated by using spectrophotometry and cyclic voltammetry respectively, while their photovoltaic performance was evaluated by a device fabrication study. The DSSCs based on IK-1 and IK-2 have demonstrated an efficiency of η = 0.37% (FF = 73%) and η = 0.79% (FF = 69%) under 100 mW cm-2 simulated AM 1.5 G solar irradiation, respectively.

    Original languageEnglish
    Pages (from-to)152-158
    Number of pages7
    JournalSynthetic Metals
    Volume199
    DOIs
    Publication statusPublished - 1 Jan 2015

    Fingerprint

    2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
    indoles
    Coloring Agents
    Bearings (structural)
    Dyes
    solar cells
    dyes
    Cyclization
    Spectrophotometry
    synthesis
    spectrophotometry
    Electrochemical properties
    Cyclic voltammetry
    reagents
    Condensation
    Solar cells
    Optical properties
    condensation
    Irradiation
    Derivatives

    Keywords

    • Dye-sensitized solar cells
    • Dyes
    • Photovoltaic
    • Push-pull structure
    • Thieno[2,3- B]indole
    • Thiophene

    ASJC Scopus subject areas

    • Electronic, Optical and Magnetic Materials
    • Condensed Matter Physics
    • Mechanics of Materials
    • Mechanical Engineering
    • Metals and Alloys
    • Materials Chemistry

    Cite this

    Irgashev, R. A., Karmatsky, A. A., Kozyukhin, S. A., Ivanov, V. K., Sadovnikov, A., Kozik, V. V., ... Charushin, V. N. (2015). A facile and convenient synthesis and photovoltaic characterization of novel thieno[2,3-b]indole dyes for dye-sensitized solar cells. Synthetic Metals, 199, 152-158. https://doi.org/10.1016/j.synthmet.2014.11.024

    A facile and convenient synthesis and photovoltaic characterization of novel thieno[2,3-b]indole dyes for dye-sensitized solar cells. / Irgashev, Roman A.; Karmatsky, Arseny A.; Kozyukhin, Sergey A.; Ivanov, Vladimir K.; Sadovnikov, Alexey; Kozik, Vladimir V.; Grinberg, Vitaly A.; Emets, Viktor V.; Rusinov, Gennady L.; Charushin, Valery N.

    In: Synthetic Metals, Vol. 199, 01.01.2015, p. 152-158.

    Research output: Contribution to journalArticle

    Irgashev, RA, Karmatsky, AA, Kozyukhin, SA, Ivanov, VK, Sadovnikov, A, Kozik, VV, Grinberg, VA, Emets, VV, Rusinov, GL & Charushin, VN 2015, 'A facile and convenient synthesis and photovoltaic characterization of novel thieno[2,3-b]indole dyes for dye-sensitized solar cells', Synthetic Metals, vol. 199, pp. 152-158. https://doi.org/10.1016/j.synthmet.2014.11.024
    Irgashev, Roman A. ; Karmatsky, Arseny A. ; Kozyukhin, Sergey A. ; Ivanov, Vladimir K. ; Sadovnikov, Alexey ; Kozik, Vladimir V. ; Grinberg, Vitaly A. ; Emets, Viktor V. ; Rusinov, Gennady L. ; Charushin, Valery N. / A facile and convenient synthesis and photovoltaic characterization of novel thieno[2,3-b]indole dyes for dye-sensitized solar cells. In: Synthetic Metals. 2015 ; Vol. 199. pp. 152-158.
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    abstract = "Two novel dyes IK-1,2 bearing the 8-alkyl-8H-thieno[2,3-b]indole unit as an electron-donating part of the push-pull system have been designed and prepared, as promising sensitizers for solar cells. The key steps of the synthesis involve the crotonic condensation of 1-alkylisatins with 2-acetylthiophene, followed by reduction of the C=C double bond and further cyclization through the Paal-Knorr reaction with the Lawesson reagent, thus leading to the formation of 2-(thien-2-yl) substituted thieno[2,3-b] indole derivatives. The optical and electrochemical properties of these dyes have been investigated by using spectrophotometry and cyclic voltammetry respectively, while their photovoltaic performance was evaluated by a device fabrication study. The DSSCs based on IK-1 and IK-2 have demonstrated an efficiency of η = 0.37{\%} (FF = 73{\%}) and η = 0.79{\%} (FF = 69{\%}) under 100 mW cm-2 simulated AM 1.5 G solar irradiation, respectively.",
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    AU - Kozyukhin, Sergey A.

    AU - Ivanov, Vladimir K.

    AU - Sadovnikov, Alexey

    AU - Kozik, Vladimir V.

    AU - Grinberg, Vitaly A.

    AU - Emets, Viktor V.

    AU - Rusinov, Gennady L.

    AU - Charushin, Valery N.

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