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Exohedral Addition Chemistry of the Fullerenide Anions C and C .
Chemistry
April 2019
Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nuremberg, Nikolaus-Fiebiger-Strasse 10, 91058, Erlangen, Germany.
A systematic screening study of the exohedral reactivity of the reduced fullerenes (fullerenides) C and C is reported. These doubly and singly negatively charged carbon cages were prepared by two-fold reduction of C with potassium, leading to K C , or by in situ monoreduction with the radical anion of benzonitrile PhCN , respectively. Several series of electrophiles, including geminal and distant dihalides, benzyl bromides, and diazonium compounds, were employed as addition partners.
View Article and Find Full Text PDF-1 Isomers of tethered bismethano[70]fullerene as electron acceptors in organic photovoltaics.
RSC Adv
May 2018
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University Nishikyo-ku Kyoto 615-8510 Japan.
Isomer-controlled [70]fullerene bis-adducts can achieve high performance as electron-acceptors in organic photovoltaics (OPVs) because of their stronger absorption intensities than [60]fullerene derivatives, higher LUMO energy levels than mono-adducts, and less structural and energetic disorder than random isomer mixtures. Especially, attractive are -1 isomers that have the closest proximity of addends owing to their plausible more regular close packed structure. In this study, propylene-tethered -1 bismethano[70]fullerene with two methyl, ethyl, phenyl, or thienyl groups were rationally designed and prepared for the first time to investigate the OPV performances with an amorphous conjugated polymer donor (PCDTBT).
View Article and Find Full Text PDFBis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control.
J Am Chem Soc
September 2015
Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
In this work, we briefly report some attempts to control regioisomeric bisadditions on Sc3N@Ih-C80 and Lu3N@Ih-C80 using the tether-controlled multifunctionalization method. We then describe the use of independent (nontethered) bis-1,3-dipolar cycloaddition reactions and the characterization of 5 new bisadducts, 3 for Sc3N@C80 and 2 for Lu3N@C80, which have never been reported before. Unexpectedly and remarkably, 4 of these compounds exhibit relatively high symmetry and 2 of these bisadducts are the first examples of intrinsically chiral endohedral compounds, due to the addition pattern, not to the presence of chiral centers on the addends.
View Article and Find Full Text PDFTethered bisadducts of C60 and C70 with addends on a common hexagonal face and a 12-membered hole in the fullerene cage.
J Am Chem Soc
June 2015
†Department of Chemistry, University of Texas at El Paso, 500 West University Avenue, El Paso, Texas 79968, United States.
The regioselective synthesis of easily isolable pure bismethano derivatives of C60 and C70 with high steric congestion is described using 1,3-dibenzoylpropane bis-p-toluenesulfonyl hydrazone as the addend precursor. When the addition occurs at two [6,6] ring junctions within the same hexagon, bisadducts with mirror symmetry are obtained for both C60 and C70. When the addition occurs at two [5,6] ring junctions in C60, a symmetrical adduct is formed, which readily undergoes photo-oxygenation and ring opening to yield a fullerene with a hole in the cage.
View Article and Find Full Text PDFThe use of tethered addends to decrease the number of isomers of bisadduct analogues of PCBM.
Chemistry
October 2010
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
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