Dynamic combinatorial discovery of a [2]-catenane and its guest-induced conversion into a molecular square host

J Am Chem Soc. 2008 Aug 20;130(33):10834-5. doi: 10.1021/ja801508q. Epub 2008 Jul 23.

Abstract

A simple water-soluble naphthalenedithiol building block is converted quantitatively into a series of octameric [2]-catenanes, composed of two interlocked molecular squares. When this mixture is re-equilibrated in the presence of an adamantyl ammonium guest, the catenanes disassemble into their macrocyclic components that bind the guest with nanomolar affinity in water.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catenanes / chemical synthesis*
  • Catenanes / chemistry*
  • Chromatography, High Pressure Liquid / methods
  • Combinatorial Chemistry Techniques / methods*
  • Cyclization
  • Magnetic Resonance Spectroscopy / methods
  • Models, Molecular
  • Molecular Structure
  • Particle Size
  • Solubility
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry*
  • Water / chemistry

Substances

  • Catenanes
  • Sulfhydryl Compounds
  • Water