Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

Yong-Chang Zhai; Shimon Oiwa; Shinobu Aoyagi; Shohei Ohno; Tsubasa Mikie; Jun-Zhuo Wang; Hirofumi Amada; Koki Yamanaka; Kazuhira Miwa; Naoyuki Imai; Takeshi Igarashi; Itaru Osaka; Yutaka Matsuo

doi:10.3762/bjoc.20.109

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

Beilstein J Org Chem. 2024 May 31:20:1270-1277. doi: 10.3762/bjoc.20.109. eCollection 2024.

Authors

Affiliations

¹ Department of Chemical Systems Engineering, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.
² Department of Information and Basic Science, Nagoya City University, Nagoya 467-8501, Japan.
³ Applied Chemistry Program, Graduate School of Advanced Science and Engineering, Hiroshima University 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan.
⁴ Institute for Advanced Fusion, Resonac Corporation, 5-1 Okawa-cho, Kawasaki-ku, Kawasaki-shi, Kanagawa 210-0858, Japan.
⁵ Institute of Materials Innovation, Institutes for Future Society, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.

Abstract

Evaporable indano[60]fullerene ketone (FIDO) was converted to indano[60]fullerene thioketone (FIDS) in high yield by using Lawesson's reagent. Three compounds with different substituents in para position were successfully converted to the corresponding thioketones, showing that the reaction tolerates compounds with electron-donating and electron-withdrawing substituents. Computational studies with density functional theory revealed the unique vibrations of the thioketone group in FIDS. The molecular structure of FIDS was confirmed by single-crystal X-ray analysis. Bulk heterojunction organic solar cells using three evaporable fullerene derivatives (FIDO, FIDS, C₆₀) as electron-acceptors were compared, and the open-circuit voltage with FIDS was 0.16 V higher than that with C₆₀.

Keywords: C60; evaporable fullerene derivatives; organic photovoltaics; organic solar cells; thioketone.

Grants and funding

This work was financially supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers 21KK0087 and 23H05443. Y.M. thanks the Takahashi Industrial and Economic Research Foundation and the Yashima Environment Technology Foundation for financial support. This work was supported by the Japan Science and Technology Agency (JST SPRING), Grant Number JPMJSP2125. The synchrotron radiation experiment was performed at SPring-8 with the approval of the Japan Synchrotron Radiation Research Institute (JASRI) (Proposal No. 2023A1758).