Presenter(s): Brian Chastain − General Science
Faculty Mentor(s): Michael Haley, Justin Dressler
Poster 21
Research Area: Natural/Physical Science (Synthetic Organic Chemistry)
Funding: University of Oregon Summit Scholarship, OSEA Guy Davis Scholarship, General Chemistry Achievement Award
The properties of molecules containing unpaired electrons have been of interest to chemists ever since the first known diradical species was synthesized in 1907. More recently in 2016, the diradical molecule diindenoanthracene (DIAn) was synthesized by the Haley group. This species is of interest because of its marked stability for a molecule exhibiting diradical character. Additionally, the ability to form a dione intermediate that can react with a wide range of nucleophiles enables us to conduct a similar study to that performed by Chase et. al. on the parent indeno[1,2-b]fluorene. In this study it was discovered that the inclusion of different groups could have strong effects on the optoelectronic properties of the molecule. Here, we explore the effect of the addition of electron-withdrawing and donating groups to DIAn, specifically examining the change in the magnitude of the HOMO-LUMO energy gap, and thus the wavelength of maximum absorption in the electronic absorption spectrum. To test the effect of the groups on the properties of DIAn, nucleophilic addition reactions have been utilized to substitute the apical carbon with electron-withdrawing and donating groups. This will allow us to determine
if there are similar trends in the optoelectronic properties between the parent indeno[1,2-b]fluorene and the anthracene extended DIAn. This study will provide insight that will allow us to further refine our design principles for the preparation of organic semiconducting molecules.