Revisiting the Dehydroannulenes

University Of Kentucky Research Foundation, Lexington KY

Investigators

Abstract

The Macromolecular, Supramolecular and Nanochemistry Program of the Chemistry Division supports Professor John E. Anthony, Department of Chemistry, University of Kentucky. Professor Anthony and his research group are synthesizing and characterizing an unusual class of molecules called annulenes, which have carbon atoms arranged in a ring form. The molecules interact in solution to form aggregates and order in the solid state. Through this aggregation the molecules are able to communicate electronically and generate interesting optical properties. Such molecules could be applied to improving solar energy harvesting, enabling the construction of flexible color displays, and improving the sensitivity of sensors. The project is providing training to graduate and undergraduate researchers not only in the field of organic synthesis and characterization, but also in the use of new materials in electronic applications such as transistors. Professor Anthony is also partnering with the current Broadening Participation in Engineering program at the university to assist in recruiting students underrepresented in science to this project. Outreach activities involving high-school students are also being pursued. The field of organic electronics is built on traditional aromatic (or heteroaromatic) ring systems. As the field pushes toward higher-performance and multi-functional materials, traditional aromatic compounds are beginning to reach their limit. This project will explore dehydroannulenes, particularly formally anti-aromatic dehydro[12]annulenes, as potential components with highly exploitable properties. Key to this project is the effort to understand and control aggregation and solid-state order, as Professor Anthony's group has demonstrated with acenes. By exploiting key functionalization strategies, new molecules are being devised that exhibit ambipolar charge transport, minimized charge-carrier anisotropy, and understand how the nature of aggregation (in solution and solid state) impact singlet fission properties. Students involved in this project (graduate and undergrad researchers, as well as interns from a local high school) are performing the full range of tasks from material conception and design all the way to screening in electronic devices. In addition, a diverse group of students through NSF Broadening Participation in Engineering are being engaged in this research.