On the prerequisites for the formation of solution complexes from [60]fullerene and calix[n]arenes: A novel allosteric effect between [60]fullerene and metal cations in calix[n]aryl ester complexes

Atsushi Ikeda, Yoshio Suzuki, Makoto Yoshimura, Seiji Shinkai

Research output: Contribution to journalArticle

132 Citations (Scopus)

Abstract

In order to find calix[n]arenes which can interact with [60]fullerene in solution we have screened a number of different calix[n]arenes by spectroscopic methods. We eventually discovered such three calix[n)arenes (15·Bu(t)·H, 16·Bu(t)·H, and 23·Bu(t)·H) which could accept [60]fullerene even in solution. They commonly possess a cone conformation and a benzene ring inclination suitable to [60]fullerene inclusion. Furthermore, it was found that calix[n]aryl ester derivatives, which cannot interact with [60]fullerene, become excellent [60]fullerene-acceptors in the presence of certain specific metal cations. This was attributed to a metal-induced conformational change to preorganize cone calixi[n]aryl esters. This phenomenon is a sort of positive allosterism, which is the first example in fullerene chemistry. We believe that these findings will open a door to new fullerene-calix[n]arene conjugate chemistry.

Original languageEnglish
Pages (from-to)2497-2508
Number of pages12
JournalTetrahedron
Volume54
Issue number11
DOIs
Publication statusPublished - Mar 12 1998

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Calixarenes
Cations
Esters
Metals
Fullerenes
Cones
Benzene
Conformations
fullerene C60
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

On the prerequisites for the formation of solution complexes from [60]fullerene and calix[n]arenes : A novel allosteric effect between [60]fullerene and metal cations in calix[n]aryl ester complexes. / Ikeda, Atsushi; Suzuki, Yoshio; Yoshimura, Makoto; Shinkai, Seiji.

In: Tetrahedron, Vol. 54, No. 11, 12.03.1998, p. 2497-2508.

Research output: Contribution to journalArticle

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