Tricyclohexylphosphine-Catalyzed Cycloaddition of Enynoates with [60]Fullerene and the Application of Cyclopentenofullerenes as n-Type Materials in Organic Photovoltaics

An Ju Wu, Po Yen Tseng, Wei Hsin Hsu, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

The tricyclohexylphosphine-catalyzed [3 + 2] cycloaddition of (E)-alkyl 5-substituted phenylpent-4-en-2-ynoates with [60]fullerene was studied. This reaction undergoes an initial 1,3-addition of phosphines toward the α-carbons of enynoates. Subsequent cycloaddition of the generated 1,3-dipoles with [60]fullerene and elimination of tricyclohexylphosphines resulted in cyclopentenofullerenes in 20-43% yields. The isolated cyclopentenofullerenes were observed to serve as n-type materials in organic photovoltaics, providing a maximum average power conversion efficiency of 3.79 ± 0.29% upon embedding with P3HT in the active layer.

Original languageEnglish
Pages (from-to)224-227
Number of pages4
JournalOrganic Letters
Volume18
Issue number2
DOIs
StatePublished - 15 Jan 2016

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