An Electrochemical Investigation into the Redox Properties of Push‐Pull Dibenzodioxins and Comparative Analysis with Analogous Heteroacenes

Abstract

A series of dibenzodioxins containing electron push-pull groups were synthesized using simple methods and their spectroscopic and redox behavior was studied. Electrochemical experiments were performed to measure the redox potentials of the substituted dibenzodioxins. The role of individual molecular subunits in tweaking the redox potential values was delineated by comparing them with the electrochemical properties of analogous heteroacenes. In many cases, our redox potentials were found to be comparably low with that of many wellknown heteroacenes.

Rapid Synthesis of Phthalonitrile based Push‐Pull Bent Dibenzodioxin and its Utility in Selective Sensing of Ferric Ions

“…The extended π‐conjugation and push‐pull arrangement through attachment of some electron‐donating groups (EDG's) and electron‐withdrawing groups (EWG's) in the system leads to decrease in the orbital energy gap [2a–f] . Over the last few years, we have developed a small library of such heteroatom containing acenes called push‐pull dibenzodioxins exhibiting moderate to good emissive properties [3a–h] . There is a 1,4‐dioxin ring acting as the weak EDG and the two nitriles, either para‐dinitrile or ortho‐dinitrile as the strong EWG in the dibenzodioxin system as seen in Figure 1 (compounds 1 and 2 respectively) [3a] .…”

“…There is a 1,4‐dioxin ring acting as the weak EDG and the two nitriles, either para‐dinitrile or ortho‐dinitrile as the strong EWG in the dibenzodioxin system as seen in Figure 1 (compounds 1 and 2 respectively) [3a] . Compound 1 has been modified by further attachment of various push and pull groups on either side of the system and studied for their photophysical and electrochemical properties [3a,h] . These molecules have also proven their potential in medicinal chemistry as in vitro anti‐cancer motifs and in bio‐imaging applications [3b–f] .…”