A novel approach to manipulate cavity size In resorcinarenes

• Main Author: Parulekar, Sumedh
• Format: Others
• Published: Scholar Commons 2006
• Subjects: Cavitand; Ring closing metathesis; Bromination; Crystal structure; NMR; American Studies; Arts and Humanities
• Online Access: http://scholarcommons.usf.edu/etd/2655; http://scholarcommons.usf.edu/cgi/viewcontent.cgi?article=3654&context=etd

Intramolecular ring closing metathesis in the presence of Grubbs' catalyst has been used as an efficient approach to synthesize bridged resorcinarenes. Octaallyl cavitands may undergo conformational changes; however bridge formation by RCM of the allyl groups gives a rigid, enforced, concave cavity capable of holding neutral molecules. This is the first report describing tandem formation of the four bridges on the upper rim of resorcinarenes. Structures of bridged resorcinarenes are confirmed by spectral analysis data.This report also describes the synthesis of polyhydroxy resorcinarenes, which have been used as metal complexing agents, sensors, receptors, molecular reaction vessels and catalytic chambers. They are able to encapsulate small neutral molecules, drug molecules inside the cavity. Such cavitands offer unique molecular platforms for host--guest chemistries, as well as new polymers and self-assembled systems.