Regioselective Synthesis of [6,6]-Phenyl-C71-Butyric Acid Methyl Esters via Sulfur Ylides for Use in Bulk Heterojunction Solar Cells

Author:

Ito Takatoshi1,Inoue Yuta2,Iwasawa Tetsuo2,Sumino Shuhei1,Matsumoto Fukashi1,Iwai Toshiyuki1,Moriwaki Kazuyuki1,Takao Yuko1,Mizuno Takumi1,Ohno Toshinobu1

Affiliation:

1. Osaka Research Institute of Industrial Science and Technology

2. Faculty of Science and Technology, Ryukoku University

Abstract

We herein report the development of a regioselective synthetic route to [70]methanofullerenes, which have potential for application as electron acceptors in solution-processed bulk heterojunction solar cells. Sterically hindered sulfur ylide, generated in situ from their corresponding sulfonium salts in the presence of 1,8-diazabicy­clo[5.4.0]undec-7-ene (DBU) as the base, smoothly reacted with [70]fullerene to afford the α-type [6,6]-phenyl-C71-butyric acid methyl ester ([70]PCBM) in high purity (up to 98%). Furthermore, we successfully demonstrated the gram-scale synthesis of [70]PCBM.

Funder

This research is partially supported by the Matching Planner Program from Japan Science and Technology Agency,

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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