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Int. J. Mol. Sci. 2014, 15(12), 22642-22660; doi:10.3390/ijms151222642

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

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Received: 8 November 2014 / Revised: 21 November 2014 / Accepted: 1 December 2014 / Published: 8 December 2014
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
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Abstract

Three dialkylamino-substituted perylene tetracarboxylic dianhydrides with different n-alkyl chain lengths (n = 6, 12 or 18), 1a1c, 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, 2a2c. Additionally, Compounds 1a1c 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. View Full-Text
Keywords: perylene tetracarboxylic dianhydrides; perylene diimides; intramolecular charge transfer; solvatochromism; Lippert-Mataga equation; density functional theory calculations perylene tetracarboxylic dianhydrides; perylene diimides; intramolecular charge transfer; solvatochromism; Lippert-Mataga equation; density functional theory calculations
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Chen, K.-Y.; Chang, C.-W. Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties. Int. J. Mol. Sci. 2014, 15, 22642-22660.

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