Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides

1-Aminoperylene bisimides (1a-1c) were synthesized under mild condition in high yields, and were characterized by FT-IR, (1)H NMR, UV-Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetric analyses. These compounds are stable up to 310 degrees C according to thermogravimetric analyses. They undergo two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Their spectroscopic properties in various conditions and complementary density functional theory (DFT) calculations are reported. (C) 2011 Elsevier Ltd. All rights reserved.