Highly electron-deficient hexaazapentacenes and their dihydro precursors

Org Lett. 2012 Aug 17;14(16):4190-3. doi: 10.1021/ol301854z. Epub 2012 Aug 2.

Abstract

Novel silylethynylated N-heteropentacenes that have three adjacent pyrazine rings at the center of a pentacene backbone are reported. These hexaazapentacenes exhibit a record low energy level of lowest unoccupied molecular orbital (LUMO) for N-heteropentacenes and thus are able to oxidize dihydroanthracene to anthracene. Their synthetic precursors are the corresponding dihydrohexaazapentacenes, which exhibit interesting H-bonding.