Selection between pinching-type and supramolecular polymer-type complexes by alpha-cyclodextrin-beta-cyclodextrin hetero-dimer and hetero-cinnamamide guest dimers

J Org Chem. 2006 Jun 23;71(13):4878-83. doi: 10.1021/jo0604686.

Abstract

Novel supramolecular complexes have been prepared from an alpha-cyclodextrin-beta-cyclodextrin hetero-dimer (alpha-CD-beta-CD hetero-dimer) and hetero-cinnamamide guest dimers, G-t-Boc and G-NH2, having adamantyl groups in aqueous solutions. On addition of the competitive guest, the supramolecular structure formed by a mixture of the alpha-CD-beta-CD hetero-dimer and G-t-Boc was found to be different from that of a mixture of the alpha-CD-beta-CD hetero-dimer and G-NH2 by the 1H NMR spectroscopy, the ROESY NMR spectroscopy, and the circular dichroism spectroscopy. The size of the supramolecular complex from the mixture of the alpha-CD-beta-CD hetero-dimer and G-NH2 is larger than that from the mixture of the alpha-CD-beta-CD hetero-dimer and G-t-Boc, which was proved by the pulse field gradient spin-echo NMR and the atomic force microscopy. These results suggest that the mixture of the alpha-CD-beta-CD hetero-dimer and G-t-Boc formed a pinching-type complex, and the mixture of the alpha-CD-beta-CD hetero-dimer and G-NH2 formed a supramolecular polymer-type complex.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cinnamates / chemistry*
  • Circular Dichroism
  • Dimerization
  • Macromolecular Substances / chemistry
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Microscopy, Atomic Force / methods
  • Models, Molecular
  • Molecular Structure
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Reference Standards
  • Sensitivity and Specificity
  • alpha-Cyclodextrins / chemistry*
  • beta-Cyclodextrins / chemistry*

Substances

  • Cinnamates
  • Macromolecular Substances
  • Polymers
  • alpha-Cyclodextrins
  • beta-Cyclodextrins
  • betadex
  • cinnamamide
  • alpha-cyclodextrin