2-Bromotetraazapentacene and Its Functionalization by Pd(0)-Chemistry.

We have synthesized a brominated N,N'-dihydrotetraazapentacene using a condensation route. Sonogashira reactions replace the Br-substituent by an alkynyl group, placed on the azaacene core. Sonogashira coupling of brominated dihydro tetraazapentacene 1H2 with alkynes and subsequent oxidation afford several functionalized TIPS-tetraazapentacene derivatives with energetically stabilized FMOs. These TIPS-TAPs are either crystalline or amorphous, depending upon their substitution pattern. [ABSTRACT FROM AUTHOR]