Halogenated benzene-1,2,3,4-tetracarboxylic diimides hold great versatility to facilitate further coupling chemistry and as a scaffold for other organic materials research. However, there have been previous challenges in their synthesis due to their structural aspects that easily facilitate unwanted Nucleophilic Aromatic Substitution (NAS) reactivity. We improved upon a previous protocol to synthesize dihalogenated benzene-1,2,3,4-tetracarboxylic diimides, finding success with a new solution-phase synthesis using acetic acid as solvent to react benzene-1,2,3,4-tetracarboxylic acids with primary amines in the liquid state. Using spectroscopic methods, we confirmed the structures of the synthesized molecules. Contrary to other published literature on well-known syntheses of conventional aromatic diimides, we discovered that it is crucial to avoid a cyclic anhydride as the diimide precursor. Furthermore, we were able to explore initial reactions of organometallic coupling are excited to continue investigating the potential for these ortho-substituted benzene derivatives to be building blocks for organic substitutes to inorganic metal-based semiconductors, as well as investigating their applications in medicinal chemistry and biomolecular engineering.

An improved halogenated benzene-1,2,3,4-tetracarboxylic diimide synthetic route

ACS Spring 2022

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