Linear acenaphthene-imide-fused pyrazinacene-quinone: synthesis and photophysical properties.

N-type organic semiconductors are of great importance for organic electronics. Nevertheless, the development of n-type organic semiconductors is far lagged than its counterpart of p-type organic semiconductors. Herein, a linear acenaphthene-imide-fused pyrazinacene-quinone (AIPQ) with high planarity is readily prepared via a two-fold condensation reaction. The incorporation of electron-withdrawing groups of imide, imine (C = N), and carbonyl (C = O) groups lowers the LUMO energy level of AIPQ to −4.12 eV, making it a promising candidate for n-type organic semiconductors. [ABSTRACT FROM AUTHOR]