New Synthesis of a Dibenzoperylene Motif Featuring a Doubly Boron–Nitrogen-Doped Bay Region

Abstract

A dibenzoperylene motif featuring a doubly boron–nitrogen-doped bay region is accessible from an aniline derivative in six steps in good overall yield. Two n-butyl groups provide the BN-doped polycyclic aromatic hydrocarbon with sufficient solubility in common organic solvents. The synthesis sequence allows installation of a second boron atom next to a weakly nucleophilic nitrogen by using a protected boron species. The title compound shows blue fluorescence, an extremely high fluorescence quantum yield, and an interesting doped bay region.

Key words

boron - chromophores - nitrogen - azaborinines - polycycles

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