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Chiral organoboron PAHs for application in organic electronics

Felix Full – Hector RCD Awardee Agnieszka Nowak-Krol

Boron-containing polyaromatic hydrocarbons (PAHs) draw increasing interest due to their appealing optical and electronic features. They are promising candidates for applications in organic electronics, e.g. OLEDs, transistors and organic solar cells. This project is focused on the synthesis of new chiral organoboron PAHs and the investigation of the impact of their chiral geometry on the operation of such devices.

This project is focused on the development of chiral boron-containing polyaromatic hydrocarbons (PAHs). While PAHs already find application in organic solar cells and transistors, there is still potential for improvement. Incorporation of heteroatoms into π-conjugated scaffolds can significantly alter the properties of a parent scaffold, improve operation of these devices and provide new functions. Despite the attractive properties of boron, helically chiral scaffolds containing this element are rare due to synthetic limitations. Therefore, a major goal of this project is to get access to this new class of compounds.

The synthesis of boron embedded PAHs is executed by a modular approach. To construct these compounds, achiral small (hetero)aromatic building blocks are cross-coupled with selected central cores, while subsequent borylation forms 3D multichromophoric arrays. A schematic illustration of this approach is shown in Figure 1.

These materials will be applied in organic electronics and photovoltaics to address the impact of chiral purity on the operation of the devices. Thus, the studies will contribute to a more comprehensive picture of the relationships between chirality and device performance.

Figure 1: A general strategy towards boron-containing chiral PAHs. R denotes alkyl, aryl or halide.