A self-assembled homooxacalix[3]arene-based dimeric capsule constructed by a pdII-Pyridine interaction which shows a novel chiral twisting motion in response to guest inclusion

A. Ikeda, H. Udzu, Z. Zhong, S. Shinkai, S. Sakamoto, K. Yamaguchi

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Abstract

A capsule-like molecule was constructed by dimerization of pyridine-containing homooxacalix[3]aryl esters utilizing a PdII-pyridine interaction when Li+ ions were bound to the ionophoric lower rims. 1H NMR spectral studies showed that the self-assembled molecular capsule 3b·(Li+)2 has a highly symmetrical D3h-structure. It was also found that this self-assembled molecular system can form capsular structures in the presence of Na+ or ammonium (R*NH3+) ions. Very interestingly, these molecular capsules are twisted into triply bridged helical structures, and chiral R*NH3+ guests included in the cavity induce a change in the (P) versus (M) ratio, resulting in high chiral induction (∼70%). These results indicate that the self-assembled molecular capsule 3b has a novel chiral factor in which the (P) versus (M) equilibrium is readily controllable by the inclusion of chiral guest molecules.

Original languageEnglish
Pages (from-to)3872-3877
Number of pages6
JournalJournal of the American Chemical Society
Volume123
Issue number17
DOIs
Publication statusPublished - Oct 8 2001

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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