A novel [60]fullerene-calixarene conjugate which facilitates self-inclusion of the [60]fullerene moiety into the homooxacalix[3]arene cavity

Atsushi Ikeda, Shigeki Nobukuni, Hiromi Udzu, Zhenlin Zhong, Seiji Shinkai

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A novel calixfullerene 1, in which a homooxacalix[3]arene moiety conjugates with a [60]fullerene moiety through a triethylene glycol chain, exhibits interesting self-complexation-decomplexation properties in response to the solvent polarity. In CDCl3, 1 exists predominantly as conformer I with a free [60]fullerene moiety and the open calixarene cavity. In CHCl3/CH3CN (1:1, v/v), however, 1 exists predominantly as the self-inclusion conformer II with the [60]fullerene moiety capped by the intramolecular calixarene moiety. This is a unimolecular event but not an aggregate formation event because the concentration effect on the stoichiometry in the (1)H NMR spectroscopy and molecular weight determination in vapor pressure osmometry are all commensurate with a unimolecular process. The complexation-decomplexation exchange rate is slower than the NMR time scale, which has enabled us to estimate the equilibrium constant [conformer II/conformer I = 0.72 in CHCl3/CH3CN (24:1, v/v) at 27 °C].

Original languageEnglish
Pages (from-to)3287-3293
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number19
DOIs
Publication statusPublished - Sep 2000

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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