(B–N)2-Heterocycles

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Research towards the synthesis of new organic structural themes and the understanding of their physical properties is as important as ever before. In this context metal-free systems have gained increasing interest in the area of materials science for, inter alia, applications in energy conversion (e.g. organic solar cells) or storage (e.g. organic flow batteries). Inspired by our work on bidentate Lewis acid catalysis as well as azobenzene switches we could show that the combination of phenyl-bisborohydride species and azobenzenes furnishes 2,3,1,4-benzodiazadiborinanes in one step, which only have been scarcely investigated. Surprisingly, when benzo[c]cinnolin was used instead of the azobenzene a novel diradical was isolated.In this project, we will systematically investigate the preparation of such stable diradicals and study their properties. Interestingly, upon treatment with pyridine, the diradical is converted into a novel (B–N)2-acene, supporting the feasibility of such structures. Hence, the second part will be devoted to the synthesis of such novel extended (B–N)2-π-systems, which will be not only be of interest for fundamental understanding of polycyclic B,N-heteroaromatics, but also show promise for applications as new materials. The project will be supported by computations.