This paper describes the synthesis of various π-extended carbazole dimers via intramolecular oxidative cyclization using a chain precursor consisting of two carbazole units bridged by a nitrogen atom. A careful selection of the reaction conditions using 2,3-dichloro-5,6- dicyano-p-benzoquinone/sulfonic acid enabled the selective synthesis of a π-extended analogue with an angular (L-shape) structure in moderate yield. The preferential positions for the bonding of the two carbazole units in this π-extended derivative were determined by performing density functional theory calculations.
