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Related Experiment Videos

Helicate, macrocycle, or catenate: Dynamic topological control over subcomponent self-assembly.

Marie Hutin1, Christoph A Schalley, Gérald Bernardinelli

  • 1Department of Organic Chemistry, University of Geneva, 30 Quai Ernest-Ansermet, 1211 Genève 4, Switzerland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 15, 2006
PubMed
Summary

Researchers created a dimeric helical macrocycle using a copper(I) reaction. This macrocycle

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Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Macrocyclic compounds and helicates are important in supramolecular chemistry.
  • Controlling the topology of self-assembled structures is a key challenge.

Purpose of the Study:

  • To synthesize novel dimeric helical macrocycles and catenates.
  • To investigate the influence of pH and molecular structure on topological outcomes.

Main Methods:

  • Aqueous reaction of 2-(2-(2-aminoethoxy)ethoxy)ethanamine, 1,10-phenanthroline-2,9-dialdehyde, and copper(I).
  • Transimination reactions with pre-formed acyclic helicates.
  • pH-dependent studies to control topology.

Main Results:

Related Experiment Videos

  • Quantitative yield of a dimeric helical macrocycle was achieved.
  • pH-dependent switching between macrocyclic and helicate topologies was demonstrated.
  • A catenate of two interlinked macrocycles was formed using a diamine with phenylene spacers.

    • Conclusions:

    • The chelate effect drives macrocycle formation.
    • pH can be used to control the assembly of different topological structures.
    • Rigid phenylene spacers favor catenate formation over single macrocycles.