A triphenylamine-derived pentaaryl fullerene undergoes an unusual oxidative dearylation under basic conditions to give tetraarylated epoxy fullerene in high yield. The structure of the product was confirmed by single crystal X-ray diffraction. A mechanism is proposed to account for the loss of the addend and the subsequent formation of the epoxide group.
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Chemistry
September 2016
Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054, Erlangen, Germany.
Azafullerenes are as yet the only synthetically available heterofullerenes. Herein, we present plausible reaction pathways towards pentaaryl azafullerenes, focusing on the reactivity of hydro-azafullerene intermediates and their regiochemistry. The X-ray structure of a β'-hydro-tetraaryl adduct is presented for the first time.
View Article and Find Full Text PDFLangmuir
December 2015
Solid State and Structural Chemistry Unit, and ‡Department of Physics, Indian Institute of Science, Bangalore 560012, India.
A study on self-assembly of anisotropically substituted penta-aryl fullerenes in water has been reported. The penta-phenol-substituted amphiphilic fullerene derivative [C60Ph5(OH)5] exhibited self-assembled vesicular nanostructures in water under the experimental conditions. The size of the vesicles was observed to depend upon the kinetics of self-assembly and could be varied from ∼300 to ∼70 nm.
View Article and Find Full Text PDFJ Phys Chem B
October 2014
ICT, UNIFESP , São José dos Campos, São Paulo 12231-280, Brazil.
We present extensive atomistic molecular dynamics simulations of the structure and stability of fullerene-based membranes. The simulations provide a molecular description of the PhK (pentaaryl[60]fullerene anions, C60Ar5(-)·K(+)) and C8K (C60Ar5(-)·K(+) with octyl substituents) membranes. Physical chemical properties and molecular organization of PhK and C8K membranes elucidate various aspects related to their formation and potential applications.
View Article and Find Full Text PDFJ Am Chem Soc
July 2013
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.
A cobalt-sulfur cluster Co8S15 with molecular formula of (C60Ar5)-Co8S15(n)Bu2-(C60Ar5) (Ar = 4-(t)BuC6H4) was selectively synthesized from a pentaaryl[60]fullerene cobalt trisulfide complex, (η(5)-C60Ar5)CoS3. The bowl-shaped steric templating fullerene ligand, as well as the metastable cobalt trisulfide moiety, played important roles in the exclusive cluster formation. X-ray crystallography, as well as electrochemical, time-resolved photophysical, and magnetic, measurements revealed a mixed-valence cluster with six cobalt(III) and two high-spin cobalt(II) centers showing reversible redox behavior and photoinduced charge separation.
View Article and Find Full Text PDFChemistry
June 2012
Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095, USA.
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