Synthesis of porphyrin-diazacrown ether and porphyrin-cryptand conjugates for fluorescence detection of copper(II) ions

Abstract

Palladium-catalyzed amination was used for the synthesis of the macrocycles containing trioxadiamine linker and the fragments of either 3,3′-disubstituted biphenyl or 2,7-disubstituted naphthalene. Catalytic macrocyclization gives diazacrown ether-based cryptand with trioxadiamine linker. The synthesized compounds were involved in Pd-catalyzed arylation of zinc meso-(bromophenyl)porphyrin to obtain polymacrocyclic conjugates bearing one or two porphyrin units. The synthesized conjugates were studied as fluorescence sensing material and molecular probes for 18 metal ions. It was found that two of them are very promising fluorescent chemosensors for copper(II) cations.