Efficient functionalizations of heteroatom-bridged calix[2]arene[2] triazines on the larger rim

(Chemical Equation Presented) Heteroatom-bridged dichlorinated calix[2]arene[2]triazines, which were synthesized from the fragment coupling reactions of cyanuric chloride and various aromatic dinucleophiles, are a unique type of platform for the construction of functional macrocyclic host molecules. Utilizing a very convenient and straightforward nucleophilic displacement reaction of dichlorinated tetraoxacalix[2]arene[2]triazine by various chelating group-containing amines, a number of functionalized tetraoxacalix[2]arene[2] triazines on the larger rim were efficiently synthesized in good yields. The resulting tetraoxacalix[2]arene[2]-triazines armed with two 2,2′- bi(pyridinyl)amino or two bis(2-pyridinemethyl)amino groups selectively formed 1:1 complexes with Cu²⁺ ion through most probably a chelating interaction effect.