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Synthesis of Quinoxaline-Based Small Molecules Possessing Multiple Electron-Withdrawing Moieties for Photovoltaic Applications

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Abstract

Three quinoxaline-based small molecules possessing multiple electron-withdrawing moieties were synthesized by the Suzuki coupling reaction for organic photovoltaic cells (OPVs). The electron-donating triarylamine units were linked to both ends of electron-accepting 2,3-diphenyl quinoxaline (DPQ) derivatives with strong electron-withdrawing trifluoromethyl (CF3) moieties to produce a reference D-A-D type small molecule of CF3Qx-0F. Furthermore, one and two fluorine atoms were additionally introduced to the 6,7-positions ofthe DPQ unit of CF3Qx-0F affording CF3Qx-1F and CF3Qx-2F, respectively. Owingto the significant contribution of the electron-withdrawing CF3 and fluorine units, all inverted-type OPVs based on three small molecules exhibited high open circuit voltages greater than 0.82 V. In addition, the power conversion efficiencies (PCEs) of the devices were gradually improved with increasing number of fluorine atoms. The highest PCE (2.82%) with a Voc of 0.88 V, a short-circuit current of 6.38 mA cm−2, and a fill factor of 50.6% was achieved from the device based on CF3Qx-2F.

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Author notes

  1. J. T. Kim and H. C. Jin equally contributed to this research.

Authors and Affiliations

  1. Department of Industrial Chemistry, Pukyong National University, Busan, 48513, Korea

    Jun Tae Kim, Sella Kurnia Putri & Dong Wook Chang

  2. Department of Polymer Engineering, Pukyong National University, Busan, 48513, Korea

    Ho Cheol Jin & Joo Hyun Kim

  3. Linz Institute for Organic Solar Cells (LIOS)/Institute of Physical Chemistry, Johannes Kepler University Linz, 4040, Linz, Austria

    Dong Ryeol Whang

Authors
  1. Jun Tae Kim
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  2. Ho Cheol Jin
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  3. Sella Kurnia Putri
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  4. Dong Ryeol Whang
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  5. Joo Hyun Kim
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  6. Dong Wook Chang
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Correspondence to Joo Hyun Kim or Dong Wook Chang.

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Footnote: The image from this article is used as the cover image of the Volume 27, Issue 12.

Acknowledgment: This research was supported by Basic Science Researches through the National Research Foundation (NRF) of Korea under program number (2018R1D1A1B07042822 and 2016R1D1A1B03930154).

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Kim, J.T., Jin, H.C., Putri, S.K. et al. Synthesis of Quinoxaline-Based Small Molecules Possessing Multiple Electron-Withdrawing Moieties for Photovoltaic Applications. Macromol. Res. 27, 1268–1274 (2019). https://doi.org/10.1007/s13233-020-8002-7

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