Regio- and stereo-selective intermolecular [2+2] cycloaddition of allenol esters with C60 leading to alkylidenecyclobutane-annulated fullerenes

Mitsuhiro Ueda*, Tsukasa Sakaguchi, Miho Hayama, Takafumi Nakagawa, Yutaka Matsuo, Aiko Munechika, Shunsuke Yoshida, Hiroshi Yasuda, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The intermolecular [2+2] cycloaddition of allenol esters, which were in situ generated by Pt-catalyzed 1,3-acyloxy migration of propargylic esters, with C60 proceeded regio- and stereo-selectively to give a novel class of alkylidenecyclobutane-annulated fullerenes. The cyclobutane-annulated fullerene derivatives have high-lying LUMO levels, which gave a high open-circuit voltage in organic solar cell applications. The observed high electron mobility provided a good fill factor compared with the PCBM-based devices.

Original languageEnglish
Pages (from-to)13175-13178
Number of pages4
JournalChemical Communications
Volume52
Issue number89
DOIs
StatePublished - 1 Jan 2016

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