Cyclic [2]pseudorotaxane tetramers consisting of two rigid rods threaded through two bis-macrocycles: copper(I)-templated synthesis and X-ray structure studies

J Am Chem Soc. 2008 Aug 20;130(33):11013-22. doi: 10.1021/ja801924y. Epub 2008 Jul 25.

Abstract

Variously substituted coordinating rigid rods have been synthesized which incorporate a central 4,7-phenanthroline nucleus attached to two 2-pyridyl groups via its 3 and 8 positions, so as to yield bis-bidentate chelates, the two-coordinating axes of the chelates being parallel to one another. Regardless of the nature of the substituents borne by the rods, the copper(I)-induced threading reaction of two such rods through the rings of two bis-macrocycles affords in a quantitative yield the 4-copper(I) threaded assembly. The [2]pseudorotaxane tetramers thus obtained have been fully characterized in solution and, for one of them, an X-ray structure could be obtained, confirming the threaded nature of the complex and providing important structural information.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Phenanthrolines / chemistry*
  • Rotaxanes / chemical synthesis*
  • Rotaxanes / chemistry
  • Stereoisomerism

Substances

  • Macrocyclic Compounds
  • Organometallic Compounds
  • Phenanthrolines
  • Rotaxanes
  • 4,7-phenanthroline
  • Copper