6533b839fe1ef96bd12a669f
RESEARCH PRODUCT
Lower rim arylation of calix[n]arenes with extended perfluorinated domains
Antonio Palumbo PiccionelloDomenico GarozzoTullio PilatiAndrea PaceSilvestre BuscemiSebastiano PappalardoMelchiorre F. ParisiGiuseppe GattusoIlenia PisagattiAndrea Pappalardosubject
Calixarenes; organofluorine derivativeChemistryPentamerOrganic ChemistryBiochemistryCrystallographychemistry.chemical_compoundTetramerDrug DiscoveryCalixareneCalixarenesSpectral dataAcetonitrileorganofluorine derivativeConformational isomerismDerivative (chemistry)description
Abstract Exhaustive O-arylation of p-tert -butylcalix[ n ]arenes 2 ( n = 4–8) with an excess of 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole 3 and K 2 CO 3 in refluxing acetonitrile provides an easy entry to a new family of perfluorinated calix[ n ]arenes 1 . The cyclic tetramer furnishes a mixture of cone , partial cone , and 1,2-alternate conformers, while the larger macrocycles afford single products. The structures of all new compounds are substantiated by NMR techniques and MALDI-TOF mass spectral data. Single-crystal X-ray diffraction studies on the pentamer derivative 1b reveal a distorted cone-in conformation of the calixarene cup.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-12-01 |