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Organic Letters

Organic Letters

IF: 4.9
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Tricyclohexylphosphine-Catalyzed Cycloaddition of Enynoates with [60]Fullerene and the Application of Cyclopentenofullerenes as n-Type Materials in Organic Photovoltaics

Published:31 December 2015 DOI: 10.1021/acs.orglett.5b03293 PMID: 26720807
An-Ju Wu, Po-Yen Tseng, Wei-Hsin Hsu, Shih-Ching Chuang*

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.

Synthesis

Benzene, 1-(1,1-dimethylethyl)-4-(1-propenyl)-
3-(4-TERT-BUTYL-PHENYL)-PROPENAL

Substances (2)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Tricyclohexyl phosphine 2622-14-2 C18H33P 470 suppliers $6.00-$1196.00
Poly(3-hexylthiophene-2,5-diyl) 104934-50-1 C10H14R2S 129 suppliers $95.00-$5595.00

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