Project Summary: 

Planarization of 3D aromatic molecules (e.g., helicenes, etc.) in solution chemistry of on metal surfaces is common and well-established process. However, the opposite process conversion of planar aromatic compounds to 3D ones is synthetically less explored, due energetic and synthetic problems. On the other hand, it constitutes an interesting and challenging synthetic problem. Therefore, the main purpose of the grant proposal is development of synthetic approaches to convert planar aromatics compounds possessing suitable functional groups to selectively decorated 3D aromatic compounds. The essential part of the planned synthetic endeavors will be focused on preparation of chiral 3D molecules. Although the target compounds will be devoid of standard elements of symmetry, thanks to the absence of a plane of symmetry. Specifically, the expected course of studies will be based on annulative reactions of the triple bonds in benzotricyclyne with various other reactants resulting in the formation of enlarged π-conjugated systems. Transformation of sp-hybridized C atoms in the triple bonds to the sp2-ones, will result in twisting of the molecular scaffold changing it to 3D one. It is expected to apply the developed methodology also to reactions with tetrabenzocyclyne. An integral part of the project will be studies of chemico-physical properties of the prepared compounds by using various experimental (absorption and emission, CPL, electrochemistry, X-ray diffraction analysis, etc.) and theoretical methods (DFT calculations, etc.). The fundamental aspects regarding feasibility of the outlined project have been already reported by us (Jacko, J.; Stas, M.; Rulíšek, L.; Císařová, I.; Kotora, M. J. Org. Chem. 2022, 87, 744750. Ir-Catalyzed Cycloaddition of Tribenzocyclyne with Biphenylenes. DOI: 10.1021/acs.joc.1c01118 ).

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