Design and Synthesis of Functionalized Organic Semiconductors

Michael Quinlan O'Sullivan
Michael Quinlan O’Sullivan

Hello! I’m Michael, a rising junior from Massachusetts (class of 2023). I attended Holliston High School and am currently majoring in Chemistry as well as Molecular Biology & Biochemistry. Here at Wes’ I enjoy going on hikes, video editing, and constantly making dumb jokes with friends. After Wesleyan, I hope to go to pursue a PhD in either Chemistry or Neuroscience.


The prevalence of organic semiconductors (OSC) in the fields of nanotechnology and photovoltaics has been rapidly increasing for the past few years. Compared to their inorganic counterparts, organic semiconductors are generally cheaper to produce and structurally more flexible; however, it is essential to note that some of the most promising OSCs have decreased charge-carrier mobility and are prone to oxidation, hindering commercialization. This research aims to combat these issues by synthesizing compounds known as phenazines that are more oxidatively resistant and will provide future avenues to synthesize similar compounds with different properties via functionalization. Phenazines contain nitrogen atoms in π-conjugated cyclic systems. These heteroatoms increase resistance to oxidation and allow for the fine-tuning of molecules with promising electronic and/or optical properties. In this research, 3 primary molecules have been designed and will be investigated: AB, ABA, and BAB. They are the result of a condensation reaction between pyrene-based quinones (the “A” component) and naphthalene diimide-based amines (NDI, the “B” component). Computational modeling using Gaussian16 has shown that the unfunctionalized versions of these molecules have HOMO-LUMO gaps between 1.9-2.6 eV, which is within the range corresponding to semiconductors. The synthesis of pyrene and tert-butyl pyrene derivatives have been successfully completed. Synthesis of the target tetraamino-NDI derivative is ongoing. Future work involves completion of the NDI derivative and subsequent condensation of the target AB, ABA, and BAB phenazine derivatives. After synthesis, the electronic properties of the target molecules will be compared to the results obtained from the computational work. Following this stage, functionalized versions of these molecules will be made to see how their electronic properties can be fine-tuned.


Michael Quinlan O’Sullivan (Chemistry)

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Thursday, July 29th 1:15-2:30pm EDT