Direct synthesis of sulfonated azacalixarenes in water

Abstract

Successive treatment of cyanuric chloride with two aromatic diamines, at least one of them sulfonated, yields water-soluble sulfonated azacalix[4]arenes which may be isolated by crystallisation. Functionalised azacalixarenes may be made by first displacing two chloro substituents from the cyclisation precursor. Attempted formation of an azacalix[6]arene led to a dimeric species for which two structures may be proposed, one of them an azacalixarene catenane.