Dibenzoindolo[1,8]naphthyridines: Synthesis and Characterization of X‐Shaped Aza[4,6]helicenes

Abstract

AbstractThis report describes a one‐pot multi‐step procedure to obtain double azahelicenes via nucleophilic fluorine substitution of 2,2‐di(2‐bromophenyl)‐1,1‐difluoroalkenes and palladium‐catalysed ring closing reaction. The developed synthesis approach allows easy diversification of substituents at all four fragments of the obtained X‐shaped aza[4,6]helicene entity. Yields range from 20 % to 60 % among 12 product examples. X‐ray single crystal analysis reveals formation of (P,P) and (M,M) enantiomer mixture of products. Optical and electrochemical properties of selected products were studied by performing UV/Vis absorption, photoluminescence and cyclic voltammetry measurements. Experimental results are supported by (TD)‐DFT, NICS and NICS2BC calculations.