Synthesis and Investigation of N,N'-benzylated Epindolidione Derivatives as Organic Semiconductors

摘要

We report how the N, N'-disubstitution of epindolidione with a benzyl group surprisingly leads to irreversibility of oxidation and thus to only n-type transport in a material with otherwise quasi-reversible reduction and oxidation and charge transport ambipolarity. Cyclic voltammetry, bulk electrolysis and UV-Vis spectroscopic methods were applied to elucidate the electrochemical reaction pathway leading to oxidative degradation and conclude that the same product that can be produced electrochemically is also found in the solid-state device. The chemical substitution of hydrogen-bonded acridone-based semiconductors can lead to substantial changes in their electrical properties, and more broadly, the electrochemistry of organic semiconductors in solution can be closely related to their solid-state charge transport phenomena.