1,7-Dinitroperylene bisimides: facile synthesis and characterization as n-type organic semiconductors

1,7-Dinitroperylene bisimides (1a-1b) and 1-nitroperylene bisimides (2a-2b) were synthesized under mild condition in high yields, and were characterized by FT-IR, 1H NMR, UV-vis, HRMS spectra, cyclic voltammetry, and thermogravimetric analyses. These compounds are stable up to 260 °C according to thermogravimetric analyses. They undergo two quasi-reversible one-electron reductions in THF at modest potentials. The nitro functionalities provide stability of n-type charge carriers by lowering the LUMO to resist ambient oxidation.