UD-Bodipy Fluorophores: A Computational Study

Boron-dipyrromethene (BODIPY) compounds are an exciting class of fluorescent molecules. Several variations on this structure exist in the literature and have been studied extensively by experimental as well as computational methods. Unfortunately, these compounds can be expensive to make and many do not contain optimal properties such as absorbance in the near-IR region of 700-1000 nm. Recent efforts in the Swavey laboratory at the University of Dayton (UD) have revealed a new class of these molecules (UD-BODIPY) with quantum efficiencies ~1, making them rare and interesting chromaphores, but still lack the desired absorbance profile. We hypothesize the properties of UD-BODIPY chemicals are related to their structure, but the relationship between structure and activity is not yet fully understood. Several UD-BODIPY’s have been prepared in the laboratory and they all posses an double benzo[e]isoindole core. UD-BODIPYs can be synthesized easily by condensation of different aldehydes to form the more complex fused ring systems. As with any synthesis, it might be faster and more efficient to screen large numbers of UD-BODIPYs in silico before their synthesis is attempted. UD-BODIPY’s will be evaluated through for suitability as fluorescent dyes in biological systems or for use in organic solar cells. We are developing a robust computational method for screening and selecting interesting UD-BODIPY compounds. The goal is to understand the influence of geometry and/or structure changes on the fluorescence performance of these chemicals. We will then use our knowledge to design new UD-BODIPYs