NSF Award
2108949
With the support of the Macromolecular, Supramolecular and Nanochemistry program in the Division of Chemistry, Dr. Brian H. Northrop of Wesleyan University will develop new synthetic approaches into semiconducting organic materials using phenazines as building blocks. Phenazines are cyclic organic molecules consisting of carbon, hydrogen and nitrogen. The alternation of pi-bonds (double bonds) in these systems enables the molecules or polymers to conduct electrons. Just like traditional semiconductors such as silicon, these materials can become conductive when one applies a voltage--as in transistors--or irradiate them with light--as in photovoltaic cells. In this work, experimental and theoretical chemistry will be used to prepare a family of phenazines derivatives containing different functionalities and reactivities. Optimized derivatives will then be assembled into various 1D- and 2D-structures potentially creating materials with unique opto-electronic properties. Successful preparation of new phenazine based materials would have potential long term scientific impact for the design of optoelectronic materials, optics and sensing. Students associated with this project will ve exposed to interdisciplinary research and, as such, be well positioned for career paths in the academic, industrial or government sectors. An introduction to polymers program and summer bridge program will be created to reach middle school students and introduce them to research in STEM (Science, Technology, Engineering and Mathematics) fields.<br/><br/>This research will focus on experimental and theoretical investigations of phenazines and the use of phenazine assembly in the design and synthesis of well-defined, pi-conjugated organic materials and macromolecules. In the first objective, experimental synthesis and analysis will be combined with first principles calculations to investigate the formation and aromaticity of simple phenazine derivatives, as well as the impact of functional groups on the favorability and reversibility of phenazine condensation reactions. The second objective will focus on the preparation of a library of ortho-phenylenediamine and ortho-quinone functionalized building blocks that will be used in the controlled assembly of one-dimensional multifunctional phenazine derivatives and oligomers. Finally, in the last objective, new knowledge from fundamental and one-dimensional phenazine studies will be applied to prepare monodisperse, two-dimensional phenazine polygons, ladders, and grids. Incorporation of phenazine units into conjugated framework is a synthetic strategy that has not been extensively explored in the field of conjugated materials. Consequently, new fundamental chemistry knowledge will be generated that could lead to design of interesting pi-conjugated materials and advancements in understanding of how phenazine affects their physical and optoelectronic properties.<br/><br/>This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.
