Boron-Functionalized pi-Conjugated Materials with Tailored Properties

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With the support of the Chemical Synthesis program of the Division of Chemistry, Professor Frieder Jäkle of the Department of Chemistry at Rutgers University-Newark will investigate conjugated materials that are functionalized with boron-nitrogen Lewis pairs. Conjugated materials are ones where electrons are delocalized easily over extended distances. They play major roles as in organic electronic devices and displays, photocatalysis, bioimaging, and therapeutics. By introducing boron into a conjugated material its electronic structure can be altered, which can result in desirable properties, for example, the absorption and emission of near-infrared light and are important characteristics for bio-imaging and biotherapeutic applications. This research addresses the need to develop new methods to prepare such compounds in order, in the longer term, to fully leverage their favorable properties in applications such as electronic materials development and catalysis, and for deployment in biomedical applications. In addition to the training of undergraduate and graduate students, high school outreach programs are planned that allow students and their teachers, including those from underrepresented groups, to experience University research first-hand, learn about modern research tools, while also being introduced to career opportunities in the science, technology, engineering, and mathematics (STEM) fields.The research project explores the functionalization of organic conjugated materials with boron-nitrogen (B-N) Lewis pairs as a means of tuning their electronic structure, photophysical properties, and chemical reactivity. In one direction, the research will target B-N Lewis pair-functionalized polycyclic aromatic hydrocarbons that feature reduced gaps between the highest occupied and lowest unoccupied molecular orbitals. Such systems are expected to absorb or emit in the near-infrared region and/or exhibit electrochromic properties. In another direction, heteroaromatic systems will be explored as potential chromophores for photoredox catalysis. Finally, macrocycles are being developed that combine luminescent, oxygen-responsive, and host-guest properties. The results are expected to offer new fundamental insights into the properties of organic materials that are functionalized with B-N Lewis pairs while also contributing to the development of luminescent, electrochromic, photocatalytic, host-guest, diagnostic and therapeutic materials.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.