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Materials 2015, 8(8), 4943-4960; doi:10.3390/ma8084943

1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Author to whom correspondence should be addressed.
Academic Editor: Harold Freeman
Received: 3 July 2015 / Revised: 29 July 2015 / Accepted: 30 July 2015 / Published: 3 August 2015
(This article belongs to the Special Issue Developments in Organic Dyes and Pigments)
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Abstract

1,6- and 1,7-regioisomers of diamino-substituted perylene tetracarboxylic dianhydrides (PTCDs) with different n-alkyl chain lengths (n = 6, 12 or 18) were synthesized and characterized by NMR spectroscopy and high-resolution mass spectrometry. These dyes are highly soluble in most organic solvents and even in nonpolar solvents, such as hexane. To the best of our knowledge, this is the first time the 1,6-diamino-substituted PTCDs (2a2c) have been obtained in pure form. The regioisomers 1a1c (1,7-) and 2a2c (1,6-) exhibit significant differences in their optical characteristics. In addition to the longest wavelength absorption band at around 674 nm, 2a2c exhibit another shoulder band at ca. 600 nm, and consequently, cover a large part of the visible region relative to those of 1a1c. Upon excitation, 2a2c also show larger dipole moment changes than those of 1a1c; the dipole moments of all compounds have been estimated using Lippert–Mataga equation. Moreover, all the dyes show a unique charge transfer emission in the near-infrared region, of which the peak wavelengths exhibit strong solvatochromism. They all exhibit one irreversible one-electron oxidation 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 rationalize their electronic structure and optical properties. View Full-Text
Keywords: diamino-substituted perylene tetracarboxylic dianhydrides; intramolecular charge transfer; near-infrared fluorescent dyes; solvatochromism; Lippert–Mataga equation; density functional theory calculations diamino-substituted perylene tetracarboxylic dianhydrides; intramolecular charge transfer; near-infrared fluorescent dyes; 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.; Tsai, H.-Y. 1,6- and 1,7-Regioisomers of Highly Soluble Amino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties. Materials 2015, 8, 4943-4960.

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