Regioselective recognition of a [60]fullerene-bisadduct by cyclodextrin

Atsushi Ikeda, Michiko Ishikawa, Ryota Aono, Jun Ichi Kikuchi, Motofusa Akiyama, Wataru Shinoda

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

The three different regioisomers of bis-N-methylfulleropyrrolidines have been separated by controlling the relative amounts of γ-cyclodextrin and dimethyl sulfoxide (DMSO) contained in solutions of these compounds. When a small amount of γ-CDx was used in a mechanochemical high-speed vibration milling apparatus, the trans-1 and trans-2•γ-CDx complexes were separated from the trans-3•γ-CDx complex. In contrast, trans-3 was extracted in a relatively high ratio with an excess of γ-CDx. The addition of DMSO to aqueous solutions of the fullerene derivative•γ-CDx complexes allowed for the three regioisomers to be obtained in high purity (>95%). The basis for the observed regioselective separation was a competition between the relative stabilities and solubilities of the complexes in the water and water-DMSO solvents. The stabilities of the complexes in water were assessed by the number of hydrogen bonding interactions between the two γ-CDx units using molecular dynamics simulations. To the best of our knowledge, this is the first reported example of the isolation of the different regioisomers of fullerene derivatives using host-guest complexes.

Original languageEnglish
Pages (from-to)2534-2541
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number6
DOIs
Publication statusPublished - Mar 15 2013
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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