Synthesis of meso-2,2’-bipyridyl-substituted calix[4]arenes and their response to metal cations

Abstract

A convenient synthetic approach to meso-substituted with 2,2’-bipyridine and 1-(pyridin-2-yl)isoquinoline residues calix[4]arenes is reported. This approach involves the reaction of generated in situ 2-lithio-calix[4]arene with 1,2,4-triazine precursor with the following aromatization of the obtained adduct, and the aza-Diels-Alder reaction of the 1,2,4-triazinyl-substituted calix[4]arene with 2,5-norbornadien or in-situ generated 1,2-dehydrobenzene. The UV/fluorescence response of thus obtained meso-pyridyl-substituted calix[4]arenes to metal cations is studied.

Keywords

• calix[4]arene
• 1,2,4-triazines
• aza-diels-alder reaction
• 2,2’-bipyridines
• visual cations detection