title: Tricyclohexylphosphine-Catalyzed Cycloaddition of Enynoates with [60]Fullerene and the Application of Cyclopentenofullerenes as n-Type Materials in Organic Photovoltaics.
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.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University , Hsinchu 30010, Taiwan, R.O.C.
authors.forename: An-Ju
authors.initials: AJ
authors.lastname: Wu
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University , Hsinchu 30010, Taiwan, R.O.C.
authors.forename: Po-Yen
authors.initials: PY
authors.lastname: Tseng
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University , Hsinchu 30010, Taiwan, R.O.C.
authors.forename: Wei-Hsin
authors.initials: WH
authors.lastname: Hsu
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University , Hsinchu 30010, Taiwan, R.O.C.
authors.forename: Shih-Ching
authors.initials: SC
authors.lastname: Chuang