Presenter: Garret Laurie – Chemistry
Faculty Mentor(s): Gabrielle Warren
Session: (In-Person) Poster Presentation
Scientific literature has seen a dramatic increase in interesting antiaromatic structures which function as a key component within organic electronics. These molecules are novel for their inherently smaller HOMO-LUMO gap but often require protection with bulky groups or aromatic ring fusion, thereby reducing the antiaromaticity. Through heterocycle fusion at the [2,3] position of s-indacene, the antiaromaticity of the structure is increased, thereby shortening the HOMO-LUMO gap further. Our group reports the naphthofuran-fused-s-indacene which shows computational promise to not only exceed the antiaromaticity of s-indacene itself, but also the previously synthesized Haley Lab indeno[1,2b]fluorene isomers. This result is examined computationally through nucleus-independent chemical shift XY calculations and experimentally via nuclear magnetic resonance spectroscopy. Synthesis of stable antiaromatic molecules are desirable targets for providing insight on the structure, bonding, and reactivity of other highly conjugated structures.