Document Type

Honors Project On-Campus Access Only


Linear aromatic diimides play an important role in building color- intense chromophores and semiconductors. In order to explore more in this area, our lab focuses on the angled isomer mellophanic diimide (MDI). Combining MDI with various reactants into heteroacenes can lead to molecules with higher electron affinities. Changing between different heteroatoms in the structure of heteroacenes provides different physical and chemical characteristics to the molecule. In this project, we focused mainly on the NOON and NNNN series of reactions, and other interesting derivatives. 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 214,638 M-1 cm-1 for oxNOON-Cl-EtHex), high quantum yield (up to 70.8% for oxNOON-H-Bn), narrowed bandgaps (down to 2.5 eV for both oxNOON-H-Ph and oxNOON-Cl-EtPh), and significantly lowered HOMO and LUMO levels.



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