Synlett 2017; 28(12): 1457-1462
DOI: 10.1055/s-0036-1588770
letter
© Georg Thieme Verlag Stuttgart · New York

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

Takatoshi Ito*a, Yuta Inoueb, Tetsuo Iwasawab, Shuhei Suminoa, Fukashi Matsumotoa, Toshiyuki Iwaia, Kazuyuki Moriwakia, Yuko Takaoa, Takumi Mizunoa, Toshinobu Ohnoa
  • aOsaka Research Institute of Industrial Science and Technology, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan
  • bFaculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan   Email: ito@omtri.or.jp
Supported by: This research is partially supported by the Matching Planner Program from Japan Science and Technology Agency, Grant / Award Number: ‘MP27115662970’
Further Information

Publication History

Received: 26 January 2017

Accepted after revision: 07 March 2017

Publication Date:
10 April 2017 (eFirst)

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.

Supporting Information