Novel Molecules and 2D Materials Derived from Highly Conjugated, Anti-Aromatic pi-Systems

Small molecule organic semiconductors are typically composed of highly conjugated, polycyclic pi-systems that possess one or more localized regions of aromaticity. Likewise, oligomeric or polymeric structures (including 2D sheets and 2D nanoribbons) based on these polycyclic molecules possess many regions of localized (usually benzenoid) aromaticity. While aromaticity imparts added stability to these molecules and 2D materials, it comes at a cost, namely reduced delocalization of pi-electron density (i.e., reduced electron mobility). We have begun designing, synthesizing and characterizing a series of novel, anti-aromatic polycyclic molecules and materials wherein an energetic driving force exists 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. The presentation will include both experimental and theoretical (DFT) results. Characterizations of molecules and 2D materials will include optical and electronic measurements. Collaborations involving 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.