Synthesis of Bifunctional Derivatives of Calix[4]arene Bearing Azidoalkyl Fragments in Cone Stereoisomeric Form

A procedure for the chloromethylation of lipophilic distally di-O-substituted calix[4]arene derivatives has been developed to prepare dichloromethyl derivatives of calix[4]arenes with long-chain alkyl fragments in cone configuration in high yields. From the chloromethylated derivatives, ammonium/imidazolium salts containing azidopropyl moieties have been synthesized in high yields. The structure of all obtained compounds has been established by 1D and 2D NMR, IR spectroscopy, and MALDI spectrometry. They can be further used as precursors of polytriazole/polyimidazole polymer species as promising carriers for metal-complex catalysis.