1,6- and 1,7-regioisomers of highly soluble amino-substituted perylene tetracarboxylic dianhydrides: synthesis, optical and electrochemical properties

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2015
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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 (2a–2c) have been obtained in pure form. The regioisomers 1a–1c (1,7-) and 2a–2c (1,6-) exhibit significant differences in their optical characteristics. In addition to the longest wavelength absorption band at around 674 nm, 2a–2c exhibit another shoulder band at ca. 600 nm, and consequently, cover a large part of the visible region relative to those of 1a–1c. Upon excitation, 2a–2c also show larger dipole moment changes than those of 1a–1c; 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.
Reference Key
chen2015materials1,6- Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;Kew-Yu Chen;Che-Wei Chang;Hsing-Yang Tsai
Journal Nature Materials
Year 2015
DOI
10.3390/ma8084943
URL
http://www.mdpi.com/1996-1944/8/8/4943
Keywords
solvatochromism intramolecular charge transfer electronics civil engineering (general)microscopydescriptive and experimental mechanics nuclear engineeringengineering (general) density functional theory calculationstechnologyelectrical engineering diamino-substituted perylene tetracarboxylic dianhydrides

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