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

doi:10.1021/acs.orglett.5b03293

Paper

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

Published Jan 15, 2016 · An-Ju Wu, Po-Yen Tseng, Wei‐Hsin Hsu

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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.

Study Snapshot

Cyclopentenofullerenes, produced through tricyclohexylphosphine-catalyzed cycloaddition of enynoates with fullerene, show potential as n-type materials in organic photovoltaics, providing a maximum power conversion

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

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Citations

Phosphine-Promoted Synthesis of Naphthoquinones Fused with Cyclopentadienyl Moiety Via Ring Expansion: Synthesis, Reactivity, and Ring Contraction Via [1,5] Sigmatropic Rearrangement

Phosphine-promoted ring expansion reactions can produce biologically interesting naphthoquinones fused with a phosphorus ylide, potentially useful in redox colorimetric materials.

Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes.

Copper-mediated radical-induced ring-opening relay cascade carboannulation reaction allows for the preparation of novel five-membered carbocycle-fused fullerenes under simple redox-neutral conditions.

[60]Fullerene-Fused Cyclopentanes: Mechanosynthesis and Photovoltaic Application.

This study presents a mechanochemical cascade reaction for producing various [60]fullerene-fused cyclopentanes, which can be applied as efficient cathode interlayers in perovskite solar cells under solvent-free and ambient conditions.

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This new method for palladium-catalyzed domino spirocyclization of [60]fullerene allows for the easy and flexible synthesis of diverse novel spirocyclic derivatives with broad substrate scope and excellent functional-group tolerance.