1,7-Diaminoperylene bisimides: Synthesis, optical and electrochemical properties

作者：Tsai Hsing Yang; Chen Kew Yu^*

来源：Dyes and Pigments, 2013, 96(2): 319-327.

DOI：10.1016/j.dyepig.2012.09.003

• 1,7-Diaminoperylene bisimides
• Blue dyes
• Intramolecular charge transfer
• Lippert-Mataga equation
• DFT calculations
• Self-assembly

A series of blue dyes, 1,7-diaminoperylene bisimides (2a-2c), was synthesized under mild condition in high yields, and was characterized by H-1 NMR, UV-Vis, HRMS spectra, cyclic voltammetry, differential scanning calorimetry, and thermogravimetric analyses. These molecules undergo an excited-state intramolecular electron transfer reaction, resulting in a unique charge transfer emission. Upon excitation, they show smaller dipole moment changes than those of the asymmetric 1-aminoperylene bisimides (4a-4c); the dipole moments of these compounds have been estimated using the Lippert-Mataga equation. Furthermore, they undergo two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Their optical properties in various conditions and complementary density functional theory (DFT) calculations are reported.

• 出版日期2013-2