Document Type

Honors Project On-Campus Access Only


Aromatic diimides (ADI) are a common class of scaffolds used for research in pharmaceuticals and organic materials. In this work, we report an improved solution-phase synthesis to a less-widely explored scaffold of a non-linear ADI called mellophanic diimide (MDI) that is reproducible and generalizable. Modifications to the aromatic core and the imide functional group can lead to interesting optical, electrochemical, and potentially biochemical properties. MDIs shares many similarities with its cousin compound, naphthalene diimide (NDI) which has shown successful interaction biomolecules and demonstrated to be a successful DNA intercalator that serves as a promising anti-cancer therapeutic. Thus, we also propose MDI has a potential to be likewise developed and researched as a therapeutic scaffold and performed initial explorations of its interaction with DNA oligomers. Additionally, other preliminary experimentation that explores MDI as a monomeric unit for coupling reactions and other chemistry to expand the family of MDIs (with substitutions at the halogen and imide sites) are detailed in the work.



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