Organic radicals are essential species found in organic batteries and light-emitting diodes. The unpaired electron in the highest occupied molecular orbital allows radicals to be highly reactive and unstable. This project aimed to utilize steric protection, π-conjugation, and heteroatom functionalization to stabilize radicals. To achieve this, we have substituted electron-poor mellophanic diimides (MDIs) with nucleophiles such as diphenylphosphino ethane (dppe) to create sterically and pi conjugation resulting in phosphonium-modified aromatic diimides. MDIs with different side chains such as phenyl, benzyl and 2-phenylethyl reacted with dppe and diphenylphosphinomethane (dppm) and then characterized with cyclic voltammetry. Results from cyclic voltammetry showed evidence of reversible redox reactions to form singly and doubly reduced states. Additionally, we have attempted the bulk formation of radicals using reducing agents such as Na2S. Instantaneous color changes formed upon reagent addition suggest the formation of radicals, which are being characterized further.

Synthesis and characterization of redox-active cationic aromatic diimides

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