Syntheses and Molecular Recognition Abilities of Functionalized Calixarenes

Takashi Arimura, Seiji Shinkai, Tsutomu Matsuda

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Calixarenes are cyclic oligomers synthesized from phenols and formaldehyde. We designed and synthesized a variety of new host molecules from calixarenes. They acted as cyclic ionophores with crown-like functions by introducing ionophoric g roups. In particular calix [5] arene and calix [6] arene with carboxylate groups acted as “super-uranophiles” exhibiting the record-breaking uranyl affinity (K = 1018.4-19.2 M-1) and uranyl selectivity (1010.6-1.7). Inclusion of organic guest moleculesi n solution was effected for the first time by using water-soluble calixarenes which had either anionic, cationic, or neutral hydrophilic groups. Chiral, water-soluble calixarenes changed their conformation upon inclusion of guest molecules, which was conveniently detected by the CD spectra and provided several lines of important information for the host-guest-type complex formation. Through these studies, it was demonstrated that the moderate rigidity and the remaining conformational freedom are important characteristics of the complex formation with calixarene-based host-molecules.

Original languageEnglish
Pages (from-to)523-534
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume47
Issue number6
DOIs
Publication statusPublished - 1989

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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