Synthesis of High Performance N-Heteroaromatic Organic Field Effect Transistors from Azides

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Tom G. Driver of the Department of Chemistry at the University of Illinois at Chicago will explore the design and execution of modular, efficient syntheses of N-heteroaromatic materials from vinyl azides using their rhodium(II)-catalyzed C-H bond amination reaction. The targeted dipyrrolothiophenes and N-heterocyclic heptacenes are two classes of low molecular weight N-heterocycles that exhibit promising properties in thin film organic field effect transistors. By making rational changes to both the N-substituent and aromatic groups, the relationship between the molecular structure and bulk physical properties of their N-heteroaromatic materials will be determined to allow the properties of thin film organic field effect transistors to be tuned.Achievement of the research goals might change the synthetic strategies used for the construction of N-heteroaromatic materials. From readily available starting materials, C-H bond functionalization efficiently establishes the N-heterocyclic core and produces an N-H bond that enables easy modification of the solubility of the material. By examining the properties of the proposed N-heteroaromatic materials, fundamental insight into the relationship between the molecular structure and bulk physical properties of these materials will be gained. The knowledge gained by these studies is anticipated to enable the rational design of materials with predictable bulk properties to advance high performance printable organic electronics. In addition, this project will serve as a fertile ground for the training of students to advance in their scientific careers. By emphasizing the participation of female and underrepresented minority students, this program will help meet the goals outlined by President's Council of Advisors on Science and Technology to transform and charge the STEM-student pipeline.