Abstract
Abstract9,9′‐Bianthryl‐based cyclic dimer and dinaphtho[c,g]carbazole derivatives were synthesized from a di(2‐anthracenyl)amine derivative via Scholl reactions. The selectivity of annulation sites was regulated by the choice of oxidants. By optimizing reaction conditions with 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone (DDQ) and MeSO3H, a cyclic dimer of 9,9′‐bianthryl units featuring a chiral structure was obtained. Enantiomers of the cyclic dimer were successfully resolved by chiral high‐performance liquid chromatography (HPLC). Circular dichroism (CD) spectra of the M,M‐isomer were analyzed using theoretical calculations based on the time‐dependent density functional theory (TD‐DFT) method. The calculations reasonably reproduced the observed CD bands and determined the absolute stereochemistry. Oxidation with FeCl3 gave a dinaphtho[c,g]carbazole derivative, where the 1‐positions of the anthracene units were fused intramolecularly. DFT calculations were further employed to predict the preferential bonding sites of the two 2‐anthryl units leading to the dinaphtho[c,g]carbazole derivative.
Published Version
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