A series of tetrahomodioxacalix[4]biscrown-n. syntheses, crystal structures, and metal binding abilities

Kwanghyun No, Han Bok Ju, Hwan Suh Il, Ook Kang Sang, Jaejung Ko, Chun Nam Kye, Seung Kim Jong

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A series of novel tetrahomodioxacalix[4]biscrowns with crown-2, crown-3, crown-4, crown-5, and crown-6 units were synthesized. Conformations of each product are dependent on the base used and their conformation stabilities. All conformations were proven by NMR spectra and/or X-ray crystal structures. The 1,3-alternate homodioxacalix[4]-biscrown-4 (4b) shows the best selectivity for K+, whereas the 1,3-alternate homodioxacalix[4] crown-5 (5) does for Cs+. Those selectivities are attributable to electrostatic interaction between the metal ion and the crown ring, as well as a π-metal complexation. However, the C-1,2-alternate conformation does not take the metal ions regardless of the crown species as a result of steric hindrance from the methylene bridge of an ArCH2Ar unit.

Original languageEnglish
Pages (from-to)6938-6941
Number of pages4
JournalJournal of Organic Chemistry
Issue number20
Publication statusPublished - 2004 Oct 1
Externally publishedYes


ASJC Scopus subject areas

  • Organic Chemistry

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