A new cryptophane receptor featuring three endo-carboxylic acid groups: Synthesis, host behavior and structural study

Christian E.O. Roesky, Edwin Weber, Torsten Rambusch, Holger Stephan, Karsten Gloe, Mátyás Czugler

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Examples of a new type of cryptophane molecule incorporating aromatic groups in the bridges (1-4) and, for the first time, being also supplied with three endo-positional ionizable carboxylic acid functions (1) have been synthesized and characterized. The cryptophane triester 2 yielded a solvate (channel inclusion compound) with trichloromethane and water, the X-ray crystal structure of which is reported. The complexation of 1 with low-molecular-weight alcohols in solution was studied, and the liquid-liquid extraction of different metal ions including alkali (Na+, Cs+), alkaline earth (Mg2+, Ca2+, Sr2+, Ba2+), and the lanthanide metal ions Eu3+ and Yb3+ in an extraction system containing metal nitrate buffer/H2O/1/CHCl3 was examined. Molecular modeling calculations of the cryptophanes 1 and 2, and of the Eu3+ complex of 1 were carried out contributing to the discussion.

Original languageEnglish
Pages (from-to)1104-1112
Number of pages9
JournalChemistry - A European Journal
Volume9
Issue number5
DOIs
Publication statusPublished - Mar 3 2003

Keywords

  • Cryptophanes
  • Molecular modeling
  • Molecular recognition
  • Solvent extraction
  • Structure elucidation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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