New scaffolds for supramolecular chemistry: upper-rim fully tethered 5-methyleneureido-5'-methyl-2,2'-bipyridyl cyclodextrins

Chemistry. 2002 Jun 3;8(11):2438-45. doi: 10.1002/1521-3765(20020603)8:11<2438::AID-CHEM2438>3.0.CO;2-A.

Abstract

Seven upper-rim fully tethered cyclodextrins (URFT-CDs) have been synthesised in a good average coupling yield using the one-step "phosphine imide" approach and their metal complexation behaviour with lanthanides and transition metals was explored. We observed that the A-TE-E light conversion process (antennae effect) occurs in the URFT-CD lanthanide complexes. A molecular redox switch based on the corresponding iron complexes is also reported. A reversible intramolecular translocation of the FeII and FeIII ions, between two distinct binding cavities has been monitored spectroscopically and achieved by chemical triggering. Finally, a negative allosteric control of ion recognition through the formation of a CD pseudocryptand is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Cations / chemistry
  • Cyclodextrins / chemical synthesis*
  • Cyclodextrins / chemistry
  • Metals / chemistry*
  • Models, Molecular
  • Oxidation-Reduction
  • Spectrum Analysis

Substances

  • Cations
  • Cyclodextrins
  • Metals