Chloro- and Trifluoromethyl Derivatives of a Pentagon-Fused C: CCl, CCl, and C(CF).

The carbon cage of -C, obeying the isolated-pentagon rule (IPR), can be transformed to the non-IPR -C cage via two successive Stone-Wales rearrangements in the course of high-temperature chlorination of C with SbCl. Two chloro derivatives, -CCl and -CCl, have been isolated by high-performance liquid chromatography (HPLC). High-temperature trifluoromethylation of the chlorination products with CFI, followed by HPLC separation, afforded a non-IPR CF derivative, -C(CF).

Three Isolated-Pentagon-Rule Isomers of C Fullerene Isolated as Trifluoromethyl Derivatives.

The family of experimentally confirmed isolated-pentagon-rule (IPR) isomers of C fullerene is extended by trifluoromethylation of a C fraction of the fullerene soot, high-performance liquid chromatography separation of CF derivatives, and a single-crystal X-ray diffraction study of C(CF) compounds with the use of synchrotron radiation. New cage isomers were revealed in C(94)(CF) and C(182)(CF) compounds, whereas isomer C(181), previously known in the adduct with nickel porphyrinate, was confirmed in C(181)(CF) derivatives. Common and special features of the addition patterns of CF groups on C carbon cages are discussed in more detail.

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene.

We survey the structure and electronic properties of the family of higher trifluoromethylated C (CF ) molecules with n=14, 16, 18, and 20. Twenty-two available compounds, of which thirteen are newly obtained and characterized, demonstrate the broad diversity of π-system topologies, which enabled us to study the interplay between the CF addition pattern and the electronic properties. UV/Vis spectroscopic and cyclic voltammetric studies demonstrate the importance of the exact addition pattern rather than the plain number of addends.

Evaporation Study of an Ionic Liquid with a Double-Charged Cation.

The evaporation of a dicationic ionic liquid, 1,3-bis(3-methylimidazolium-1-yl)propane bis(trifluoromethanesulfonyl)amide ([C(MIm)][TfN]), was studied by Knudsen effusion mass spectrometry. Its evaporation is accompanied by a partial thermal decomposition producing monocationic ionic liquids, 1,3-dimethylimidazolium and 1-(2-propenyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)amides, as volatile products. This decomposition does not affect the vaporization characteristics of [C(MIm)][TfN], which were established to be as follows.

Tightly Bound Double-Caged [60]Fullerene Derivatives with Enhanced Solubility: Structural Features and Application in Solar Cells.

A series of novel highly soluble double-caged [60]fullerene derivatives were prepared by means of lithium-salt-assisted [2+3] cycloaddition. The bispheric molecules feature rigid linking of the fullerene spheres through a four-membered cycle and a pyrrolizidine bridge with an ester function CO R (R=n-decyl, n-octadecyl, benzyl, and n-butyl; compounds 1 a-d, respectively), as demonstrated by NMR spectroscopy and X-ray diffraction. Cyclic voltammetry studies revealed three closely overlapping pairs of reversible peaks owing to consecutive one-electron reductions of fullerene cages, as well as an irreversible oxidation peak attributed to abstraction of an electron from the nitrogen lone-electron pair.