Heterodinucleating macrocyclic compounds designed for electrochemical recognition

Abstract

This paper presents the electrochemical recognition properties of a series of redox-active ionophores containing two distinct complexing cavities: a Schiff base ligand complexed with Ni II, Cu II or Fe III and locked by a flexible polyoxyethylene chain of variable size. Their electrochemical recognition behavior was manifested by the emergence of a new cyclic voltammetry signal or by a progressive redox potential shift upon complexation of their crown ether-like moiety by alkali and alkaline earth metal cations, ammonium cation and protonated dopamine. UV–vis and FAB-MS experiments confirmed the formation of complexes between these receptors and the surveyed cations. Preliminary results have shown that gold electrodes modified by reaction with a receptor containing a thioether group exhibit electrochemical recognition properties similar to those found in homogeneous solution.