Tuning Antiaromaticity and Diradical Properties in Diarenoindacenes, Diindenoacenes, and Related Quinoidal Scaffolds

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With this award, the Chemical Synthesis Program of the NSF Chemistry Division is supporting the research of Professor Michael Haley of the University of Oregon who is synthesizing molecules known as indenoacenes and arenoindacenes. Professor Haley and his research group construct these compounds with systematic structural differences to answer fundamental questions about how these changes affect the electronic and material properties of these compounds. A key goal is to develop simple methods to construct these compounds in order to study their characteristics. Examination of the optical, electronic, and/or magnetic properties of these molecules then determines how they can be tuned and optimized for use in optoelectronic devices such as organic field effect transistors and organic photovoltaics. Professor Haley and his research group collaborate with material scientists, host visiting scientists from primarily undergraduate institutions for extended stays in their laboratory, and have continued substantial involvement of a diverse group of undergraduates in their research activities.Non-benzene-based conjugated systems, such as indenofluorenes (IFs), have been recognized for their potential as organic semiconductors characterized by low energy valence shells and a small band gap. This project aims to create extended IF structures and IF derivatives with heterocyclic groups to better understand the singlet-triplet gap in these diradical systems and to compare to the original IF system. The team also constructs novel asymmetric IF compounds to determine the effect of the loss of symmetry on fundamental properties. The molecules prepared in these studies present opportunities for practical applications in the areas of nanotechnology and low-cost electronics. This project also serves as an excellent training ground for graduate and undergraduate researchers with broad experiences in organic synthesis, computational chemistry, crystallography, and understanding the fundamental relationship between molecular structure and electronic properties.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.