Dynamic Electrochemistry of Anthanthrone.

Abstract

In this investigation, we present a “nanographene” based on the low-cost commercially available 4,10-dibromoanthanthrone building block, where the anthanthrone core can be viewed as a fusion of two anthracene moieties with lateral functionalization. The chemical and physical properties of this molecule stand in sharp contrast with the present anthracene subunit.

We have studied the dynamic electrochemistry from two derivates of anthanthrone where the research depends on the radical of peripheral phenyl groups. In this case, we compared the changes that produce a donor group and acceptor group respectively. In both cases, the neutral molecule has a butterfly shape due to the steric congestion between the protons at the peri position of the quinoidal anthanthrone core, which possess a nonplanar folded geometry, and the protons from the peripheral phenyl groups. However, when two electrons are subtracted, exist a core aromatization and planarization, this provides a stable flat shape.

We show the existence of two conformational states through cyclic voltammetry, electrochemistry and variable temperature chemistry oxidation. We demonstrate the fast or slow equilibrium between both geometries depending on the radical of peripheral phenyl groups (donor or acceptor).