Diazapentacenes from Quinacridones

Bis(silylethynylated) 5,7‐ and 5,12‐diazapentacenes were synthesized from cis‐ and trans‐quinacridone using protection, alkynylation and deoxygenation. The solid‐state packing of the targets is determined by choice and position of the silylethynyl substituents. The position of the substituents and nitrogen atoms influence the optical properties of the targets.
Piecing together a diazaacene: Starting from linear cis‐ and trans‐quinacridones, the synthesis, characteristics and stability of four diazapentacenes are reported leading to a design rule for 12,14‐alkynylated heteroacenes for organic electronics (see figure).