Related Experiment Video
Updated: Jun 1, 2025
Preparation and Characterization of C60/Graphene Hybrid Nanostructures
Published on: May 15, 2018
Chlorination-Supported Shrinkage of C60 Fullerene to Non-classical C58 Cages
Victor A Brotsman1, Nadezhda B Tamm1, Maria P Kosaya1
1Department of Chemistry, Moscow State University, 119991, Moscow, Leninskie gory 1-3, Russia.
Abstract:
We provide important novel insights into skeletal transformations of fullerene by reporting new cases of cage shrinkage in the most abundant C60 fullerene via a C2 loss. High-temperature (400-500 °C) chlorination of IPR C60 with SbCl5 or SbCl5/SbCl3 mixtures predominantly gives non-IPR C60Cln compounds via Stone-Wales rearrangements, but the present study further reveals non-classical C58Cln chlorofullerenes as by-products. The new C58(NC1)Cl20 and C58(NC1)Cl24 chlorides have been isolated by air-free HPLC and structurally characterized by X-ray crystallography. Their non-classical carbon cages feature one heptagon, two pairs of fused pentagons, one triple-pentagon junction, and one quartet of sequentially fused pentagons. However, the chlorination patterns and molecular shapes of C58(NC1)Cl20 and C58(NC1)Cl24 are essentially different. We propose the likely multistep transformation pathways toward the new compounds and further report the chlorination-promoted formation of chlorofullerenes with still smaller fullerene cages.
More Related Videos
13:58Probing C84-embedded Si Substrate Using Scanning Probe Microscopy and Molecular Dynamics
Published on: September 28, 2016
08:44Measurements of Long-range Electronic Correlations During Femtosecond Diffraction Experiments Performed on Nanocrystals of Buckminsterfullerene
Published on: August 22, 2017
Related Concept Videos
02:11Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
02:02Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
02:30Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
02:29Conformations of Cycloalkanes
02:46Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.