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Synthesis of pyrrolidinofullerenes and their applications as an n-type component in organic transistors and polymer solar cells

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Abstract

We synthesized pyrrolidinofullerenes functionalized with an electron donor or acceptor group via Prato reaction. Their structures were studied using 1H-NMR, FT-IR and MALDI-TOF mass spectrometry. The electronic energy levels were calculated using quantum chemical calculation based on the density functional theory, showing that the lowest unoccupied molecular orbitals were in the range of −3.7 and −3.9 eV. The electron mobility of one of the fullerene derivatives was as high as 0.05 cm2/(V s), suggesting that pyrrolidinofullerenes can be promising n-type semiconductors. The fullerene derivatives were also blended with P3HT to fabricate bulk heterojunction polymer solar cells, and the performance of solar cells as a function of structural variations of the fullerene derivatives was investigated.

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Acknowledgments

This work was supported through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT, and Future Planning (NRF-2014M3A7B4051749) and by the Ministry of Education (NRF-2014R1A1A2058289).

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Authors and Affiliations

  1. School of Chemical Engineering and Materials Science, Chung-Ang University, Seoul, 156-756, Korea

    Heeseok Song, Kimyung Kim, Hyeok Jo Jeong, Soo Young Kim & Felix Sunjoo Kim

  2. Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul, 133-791, Korea

    Jongwan Choi & Nakjoong Kim

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  1. Heeseok Song
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  2. Jongwan Choi
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  3. Kimyung Kim
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  4. Hyeok Jo Jeong
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  7. Felix Sunjoo Kim
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Correspondence to Felix Sunjoo Kim.

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Song, H., Choi, J., Kim, K. et al. Synthesis of pyrrolidinofullerenes and their applications as an n-type component in organic transistors and polymer solar cells. Polym. Bull. 73, 2477–2484 (2016). https://doi.org/10.1007/s00289-016-1675-6

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