Resorcinarenes as synthetic receptors

ORGN 585

Liam C. Palmer, Masamichi Yamanka, Alexander Shivanyuk, and Julius Rebek Jr. The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Rd, MB26, La Jolla, CA 92037
The host/guest complexes of resorcinarenes are re-examined in solution through modern spectroscopic methods. The sizes of the assemblies are determined by NMR diffusion studies and the guest exchange rates are measured by EXSY spectroscopy. For small guests such as glutaric acid and cyclohexanediols, the resorcinarene assembles as a hexameric host and encapsulates six guests. For mid-size guests, three molecules are inside and for large guests a single molecule is encapsulated in the hexameric host. The energetic barriers to exchange have also been investigated.

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