Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix[4]arenes.
Upper rim substituted tetraiodo calix[4]arenes are coupled to a variety of acrylamides using the palladium catalysed Heck reaction. Tetra-acrylamido upper rim substituted calix[4]arenes are obtained in good yields with exceptionally high stereoselectivity, to produce the all-trans isomers. Tetra-acrylamido calix[4]arenes derived from secondary acrylamides are shown to dimerise via eight hydrogen bonds to form dimeric capsules, which are able to include small organic molecules.
Kuhnert
Nikolai
N
Supramolecular and Biomolecular Chemistry Laboratory, School of Biomedical and Molecular Sciences, The University of Surrey, Guildford GU2 7XH, UK. n.kuhnert@surrey.ac.uk
Le-Gresley
Adam
A
D000178:Acrylamides / Q000737:chemistry*; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry*; D019281:Dimerization; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*
D000178:Acrylamides; D010636:Phenols; C121325:calix(4)arene; D047250:Calixarenes