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

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 position were successfully converted to the corresponding thioketones, showing that the reaction tolerate...

Full description

Saved in:
Bibliographic Details
Published inBeilstein journal of organic chemistry Vol. 20; no. 1; pp. 1270 - 1277
Main Authors Zhai, Yong-Chang, Oiwa, Shimon, Aoyagi, Shinobu, Ohno, Shohei, Mikie, Tsubasa, Wang, Jun-Zhuo, Amada, Hirofumi, Yamanaka, Koki, Miwa, Kazuhira, Imai, Naoyuki, Igarashi, Takeshi, Osaka, Itaru, Matsuo, Yutaka
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 31.05.2024
Subjects
c60
Chemistry
evaporable fullerene derivatives
Letter
organic photovoltaics
organic solar cells
thioketone
evaporable fullerene derivatives
organic solar cells
thioketone
C60
organic photovoltaics
Online AccessGet full text

Cover

More Information
Summary: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 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, C ) as electron-acceptors were compared, and the open-circuit voltage with FIDS was 0.16 V higher than that with C .
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.20.109