Imagining a World Full of Organic Semiconductor Molecules and 2D Electronic Materials Deprived of Aromatic Stabilization

Acenes are composed of linearly fused, fully conjugated six-membered rings in which only one of the rings may possess an aromatic sextet with the associated benzenoid stabilization. This interesting structural feature imparts quinoidal character and highly interesting electronic properties to large acenes, properties that most other polycyclic aromatic hydrocarbons lack including unusually small HOMO-LUMO gaps and high charge carrier mobilities. In this presentation, the synthesis and characterization of functionalized, soluble, photooxidatively resistant acenes and their associated 2D nanosheets and 2D nanoribbons will be described.

Once the connection between structures that are largely devoid of benzenoid stabilization and interesting electronic properties is made, the next logical step is to study molecules and 2D materials that are largely if not completely devoid of benzenoid stabilization. We have begun imagining, designing, synthesizing and characterizing highly conjugated polycyclic molecules and 2D materials that are deprived of benzenoid stabilization. Instead, they possess either quinoidal, non-aromatic pi-systems or formally anti-aromatic pi-systems. Within the anti-aromatic polycyclic molecules and 2D materials exists an energetic driving force to delocalize pi-electron density in order to remove localized regions of unfavorable anti-aromaticity. In order to stabilize said structures such that they can be prepared and studied, special substituent effects are employed.

This presentation will describe our progress to date. Experimental results will be combined with theoretical (DFT) calculations. Characterizations of molecules and 2D materials will include optical and electronic measurements.

Collaborations with dreamers working on optoelectronic devices of all kinds including organic photovoltaics (OPVs), organic light emitting devices (OLEDs), organic semi-metals, sensors, UV-vis and NIR camouflage and dark matter detection are actively sought before, during and after the meeting. Imagine all the electrons, moving freely throughout a 2D sheet. You may say we are dreamers, but we’re not the only ones. We hope that some day you'll join us, and the world beyond graphene will live as one.