Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties

International Journal of Molecular Sciences

Kew-Yu Chen¹  Che-Wei Chang² 

[1] Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan; E-Mail

关键词: perylene tetracarboxylic dianhydrides;    perylene diimides;    intramolecular charge transfer;    solvatochromism;    Lippert-Mataga equation;    density functional theory calculations;   

DOI  :  10.3390/ijms151222642

来源: mdpi

【 摘 要 】

Three dialkylamino-substituted perylene tetracarboxylic dianhydrides with different n-alkyl chain lengths (n = 6, 12 or 18), 1a–1c, were synthesized under mild conditions in high yields and were characterized by ¹H NMR, ¹³C NMR and high resolution mass spectroscopy. Their optical and electrochemical properties were measured using UV-Vis and emission spectroscopic techniques, as well as cyclic voltammetry (CV). This is the first time that the structures and the properties of monoamino-substituted perylene tetracarboxylic dianhydrides have been reported. These molecules show a deep green color in both solution and the solid state and are soluble in most organic solvents. They all show a unique charge transfer emission in the near-infrared region, and the associated peaks exhibit solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show slightly larger dipole moment changes than those of corresponding perylene diimides, 2a–2c. Additionally, Compounds 1a–1c undergo two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory calculations performed on these chromophores are reported in order to gain more insight into their molecular structures and optical properties.

【 授权许可】

CC BY   
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