Through-Space Communication Effects on the Electrochemical Reduction of Partially Oxidized Pillar[5]arenes Containing Variable Numbers of Quinone Units.

The electrochemical reduction of five partially oxidized pillar[5]arenes containing variable numbers (1-5) of quinone units was investigated in acetonitrile and dichloromethane solutions. The cathodic voltammetric behavior of all the macrocyclic compounds containing two or more quinone units indicates the existence of detectable levels of electronic communication between them. We have also investigated these compounds and their reduced forms using DFT computations. Our computational results indicate the presence of through-space communication between quinone units.