“Antiaromatic Organic Semiconductors”, Prof. Michael Haley, Chemistry
Polycyclic hydrocarbons that possess extended pi-conjugation are of great interest because of environmental concerns and technological usages. Most studies have focused on acenes and derivatives, molecules that are susceptible to oxidative and photolytic degradation; thus, there is a pressing need for alternative materials that do not degrade. We focus on molecules based on the indenofluorene (IF) skeleton. We have adapted and/or developed methods for the assembly of fully conjugated IF derivatives and explored the material properties. We have prepared IFs (gram quantities) with good overall yields and in excellent purity. We are exploiting IFs via a combined experimental (Oregon), physical (Spain), and theoretical (Japan) approach, directed towards use of IFs as organic semiconductors in devices.
Our REU student will help construct and study additional IF scaffolds and optimize designs for semiconducting behavior. Our syntheses are modular (think molecular level Legos®) with readily available starting materials; thus, in 10 weeks it is definitely possible for the student to construct new scaffolds and characterize the molecules by traditional spectroscopic techniques (NMR, IR, UV-vis, MS) as well as more elaborate methods (x-ray crystallography, fluorescence, EPR).