Document Type

Honors Project On-Campus Access Only


Aromatic diimides make up a common class of molecular organic semiconductor materials. With modifications to the aromatic core and the imide functional group, interesting optical and electrochemical properties can be achieved from the parent compounds. However, minimal research has been done on the smallest benzene diimides. Here, we report the synthesis of an unexplored non-linear aromatic diimide motif mellophanic diimide (MDI), which underwent nucleophilic substitutions to afforded several heteroacene chromophores. These hetero- and azaacenes were investigated through UV-vis and fluorescence spectroscopy, and density functional theory calculations. The MDI derivatives were found to exhibit high molar absorptivities (up to 39,700 M-1 cm-1), high quantum yield (up to 72.2%), narrowed bandgaps (down to 2.0 eV), and significantly lowered LUMO levels (down to 4.5 eV).



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