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, 1H NMR, UV–Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetric analyses. These compounds are stable up to 310 °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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 1-Aminoperylene bisimides were synthesized under mild condition in high yields. ► These molecules undergo an exicted-state intramolecular electron transfer reaction, resulting in a unique charge transfer emission. ► They display good thermal stability as well as good optical stability and reversible redox properties.