Novel molecular receptors based on a thiacalix[4]arene platform. Preparations of the di- and tetracarboxylic acid derivatives and their binding properties towards transition metal ions

Nobuhiko Iki, Naoya Morohashi, Fumitaka Narumi, Toyohisa Fujimoto, Tomohiro Suzuki, Sotaro Miyano

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Novel molecular receptors, cone- and 1,3-alternate-tetracarboxylic acid (3) and syn-A,C-dicarboxylic acid (5), were prepared by hydrolysis of the ester moiety of the tetra- (2) and di-ethers (4), which had been synthesized by regio- and conformation-selective O-alkylation of the phenolic oxygens of thiacalix[4]arene (1) with ethyl bromoacetate. The binding ability of cone- and 1,3-alternate-3,syn-5, as well as cone-shaped, methylene-bridged tetracarboxylic acid (9) toward transition metal ions was investigated by solvent extraction to show that the selectivity for the ions depends upon the bridging sulfur, carboxylate group, and the conformation.

Original languageEnglish
Pages (from-to)7337-7341
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number41
DOIs
Publication statusPublished - 1999 Oct 8

Keywords

  • Alkylation
  • Calixarenes
  • Complexation
  • Sulfides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Novel molecular receptors based on a thiacalix[4]arene platform. Preparations of the di- and tetracarboxylic acid derivatives and their binding properties towards transition metal ions'. Together they form a unique fingerprint.

Cite this