Aromatic diimides are fascinating molecules because they are chemically and thermally stable compounds that can undergo reversible redox reactions to generate radical species that intensely absorb light. These qualities give these molecules potential applications in the fields of molecular electronics, optics, and spintronics. However, one challenge specific to the radical anions of aromatic diimides is they are easily oxidized at low potentials in the presence of O<sub>2</sub>. To address this issue, we hypothesize that altering the geometric orientation of the imide groups on the aromatic core will change the molecule’s electronic properties by bringing the imide groups closer together. Our research is focused first on investigating the angled structural isomer of pyromellitic diimide, known as mellophanic diimide. We have successfully synthesized derivatives of this diimide and studied their reduction potentials using cyclic voltammetry and computational methods. Efforts to synthesize the chlorinated and brominated versions of these molecules have also been attempted in order to investigate how halogenation affects the stability of the radical anions of these molecules.

Synthesis and characterization of angled aromatic diimides

2019 Spring National Meeting

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