Borane Modification of Polycyclic Aromatic Hydrocarbons

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The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Frieder Jaekle. Professor Jaekle is a faculty member in the Department of Chemistry at the Newark Campus of Rutgers University. He is developing new conjugated materials called polycyclic aromatic hydrocarbons (PAHs) that contain boron-containing units. The presence of the boron enhances the potential for the PAHs to serve as materials in optical and electronic devices. To this end, PAHs have proven to be effective platforms for building organic electronics, imaging, sensors, molecular switches, etc. In these settings, their performance is improved when the materials are "doped" with either electron-rich donor or electron-poor acceptor atoms that enhance conductivity. While the doping of PAHs with nitrogen and sulfur (both donors) has been studied extensively, research into systems with other heteroatoms remains less developed. Boron is very interesting as its electron-poor (acceptor) character can result in new, desirable properties for opto-electric devices. Professor Jaekle and his students are well-positioned to make and study the boron doped PAHs in order to fully develop their potential. The project also contributes to the training of a diverse group of students in an interdisciplinary research environment at the interface of organic, inorganic and materials chemistry. Another goal is to bring together researchers from different backgrounds in pursuit of new conjugated hybrid materials through organization of symposia, international collaborations, and broad dissemination of new knowledge in this field.The specific aims of the research are to: (1) develop regioselective methods for the targeted functionalization of PAHs at their periphery via Lewis base-directed electrophilic C-H borylation; (2) develop new approaches to incorporate multiple tricoordinate boron centers into the framework of PAHs; (3) investigate the effect of boron doping/functionalization on the electronic structure, photophysical properties, and chemical reactivity. New synthetic tools are developed that provide access to unique functional pi-conjugated systems with tailored properties. Strategic placement of boranes at well-defined positions in the periphery or framework of PAHs is expected to dramatically alter their electronic structure. The preparation of the new pi-conjugated hybrids is anticipated to lead to new materials with desirable optical, electronic, stimuli-responsive and sensory properties. The research is complemented by efforts to involve students from underrepresented groups, to engage in international and interdisciplinary collaborations, and to provide a forum for scientific exchange for researchers in the field of organic-inorganic hybrid materials.