Dr. Brian Northrop Receives NSF Grant

Northrop’s proposal, titled “Phenazine chemistry as a means of assembling multifunctional π-conjugated organic materials” is motivated by the desire to understand how the structure, functionality, and dimensionality of π-conjugated organic materials impacts their physical, optical, redox, and electronic properties. Toward this fundamental goal he and his students will use the condensation reactions between ortho-phenylenediamine derivatives with ortho-quinone compounds to prepare multifunctional phenazine derivatives. Phenazines are example N-heteroacenes that, similar to their hydrocarbon acene analogues, exhibit desirable electronic and optoelectronic properties. Phenazines, however, are more stable, better electron acceptors (n-type materials), and more synthetically modular. The majority of phenazine derivatives synthesized to date have been linearly functionalized azaacenes while very few examples of organic materials combining phenazine and other π-conjugated functionalities are known. Developing a thorough understanding of phenazine assembly and integration into multifunctional molecules will lead to entirely new classes of organic electronic materials and significantly advance our ability to investigate fundamental relationships between size, functionality, lattice topology, and dimensionality on the properties of π-conjugated materials. The principle objectives of the proposed research are to: (1) combine experimental synthesis and 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; (2) synthesize a library of o-phenylenediamine and o-quinone functionalized building blocks that will be used in the controlled assembly of one-dimensional multifunctional phenazine derivatives and oligomers; (3) apply new knowledge from fundamental and one-dimensional phenazine studies to prepare monodisperse, two-dimensional phenazine ladders and grids. The phenazine-based multifunctional materials are expected to have unique semiconducting and optoelectronic properties with potential applications as organic field-effect transistors, photovoltaics, light-emitting diodes, and sensors.