Conjugated Hybrids: Functionalization of Polyaromatic and Pi-Conjugated Systems with Group 13 Elements

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In this project funded by the Chemical Synthesis Program of the NSF Chemistry Division, Professor Frieder Jaekle develops new conjugated hybrid materials that contain electron-deficient Group 13 elements (boron, aluminum, gallium, and indium). Conjugated organic materials enjoy ubiquitous applications in organic electronics, sensory materials, and supramolecular chemistry. This research aims to take advantage of recent advances in the field of Main Group Chemistry for the development of new types of conjugated hybrid materials. Organoborane groups offer electron-acceptor effect that are useful in new solution-processible materials for light emitting devices (LEDs), field-effect transistors (FETs), and photovoltaics (OPVs) - applications where acceptor materials remain in high demand. In addition, Lewis acidic organoboranes show promise as sensors for anions and other toxic small molecules. Selective boron-silicon and boron-tin exchange chemistries, Lewis base-directed electrophilic aromatic substitutions, and strategies for borenium cation formation are exploited to prepare new classes of pi-conjugated materials that are expected to exhibit: (i) strong electron-acceptor character, (ii) charge transfer and two-photon absorption properties, and (iii) a propensity for assembly on surfaces or interaction with other carbon nanomaterials. The project contributes to the training of a diverse group of students in an interdisciplinary research environment. A special focus is placed on the training of students from groups underrepresented in chemistry (e.g. American Chemical Society Project SEED high school students). Students benefit from collaborations with physical chemists in the US and Germany. In addition, Professor Jaekle organizes symposia and conferences such as the annual "Boron in the Americas" meeting.