Synthesis and self-inclusion of bipyridine-spaced cyclodextrin dimers

Hubertus F M Nelissen; Martinus C Feiters; Roeland J M Nolte

doi:10.1021/jo0256641

Synthesis and self-inclusion of bipyridine-spaced cyclodextrin dimers

J Org Chem. 2002 Aug 23;67(17):5901-6. doi: 10.1021/jo0256641.

Authors

Hubertus F M Nelissen¹, Martinus C Feiters, Roeland J M Nolte

Affiliation

¹ Department of Organic Chemistry, Nijmegen Science Research Institute of Matter, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.

PMID: 12182620
DOI: 10.1021/jo0256641

Abstract

The synthesis and conformational behavior of two cyclodextrin dimers containing aromatic bipyridine spacers is presented. The proton NMR spectra of these dimers in aqueous solution show a doubling of signals in the aromatic region due to complete or partial self-inclusion of the spacer. The degree and the strength of self-inclusion is dependent on the substitution pattern of the bipyridine unit. This unexpected difference in the self-inclusion behavior is revealed by 2D NOESY and circular dichroism spectra.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

2,2'-Dipyridyl / chemical synthesis*
2,2'-Dipyridyl / chemistry*
Chemistry, Organic / methods*
Circular Dichroism
Cyclodextrins / chemical synthesis*
Cyclodextrins / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure

Substances

Cyclodextrins
2,2'-Dipyridyl