Monitoring the thermodynamically-controlled formation of diimide-based resin-attached rotaxanes by gel-phase HR MAS 1H NMR spectroscopy

Org Biomol Chem. 2008 Jan 21;6(2):278-86. doi: 10.1039/b716325h. Epub 2007 Dec 6.

Abstract

The thermodynamically controlled self-assembly of rotaxane and pseudorotaxane systems consisting of (i) a naphthodiimide thread unit terminated at one end with a pyridine ligand, and covalently linked at the other to a gel-phase polystyrene resin support, (ii) a dinaphtho-crown ether shuttle unit, and (iii) a ruthenium carbonyl metalloporphyrin stopper unit, is investigated by high resolution magic angle spinning proton (HR MAS 1H) NMR spectroscopy. The effects of variable concentration of the solution-phase components, the temperature, and added Li+ and Na+ ions are described, and the limitations of the technique are addressed. The dynamic behaviour is compared directly to the solution-phase analogues, where a bulky stopper group is substituted for the polystyrene resin bead.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Composite Resins / chemistry*
  • Gels / chemistry
  • Imides / chemistry*
  • Magnetic Resonance Spectroscopy / methods*
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Structure
  • Protons
  • Reference Standards
  • Rotaxanes / chemical synthesis*
  • Rotaxanes / chemistry
  • Solutions / chemistry
  • Thermodynamics*

Substances

  • Composite Resins
  • Gels
  • Imides
  • Protons
  • Rotaxanes
  • Solutions