Synthesis of novel calix[4]arenes containing one and two substituents on the "upper rim"

Procedures are described for the removal of the p-butyl groups from p-tert-butylcalix[4]arene and the introduction of benzoyl, nitro, amino and acrylamido groups to yield a series of mono- and bis-substituted compounds on the "upper rim" with potential possibility to polymerized with other monomers. These compounds have been characterized by IR, ¹H NMR, elemental analysis and ESI-MS. As the upper rim of the calix[4]arene, which has the site group of polymerization, can be linked into the chains of the polyimides, the ultimate goal of the project is to find a new application for the well established binding properties of calix[4]arene and to develop polyimides that are suitable for the recovery of metal ions from waste water, gas separation and ion-specific electrodes.