Abstract
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.
Highlights
The synthesis of highly soluble Perylene diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) derivatives is very important for process ability and for the preparation of their thin films to be used in optoelectronics applications, such as organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs) and organic solar cells (OSCs)
PTCD-based chromophores available for designing systems for colorful dyes and charge transport, we report here the detailed synthesis and characterization of monoamino-substituted PTCDs (1a–1c), shown in Scheme 1
The synthesis of 1a–1c started from an imidization of perylene dianhydride 6 and cyclohexylamine in the presence of acetic acid, followed by the mononitration of perylene diimide 5, giving a nitro compound 4
Summary
Perylene diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) have received considerable attention due to their potential applications in molecular electronic and optical devices, such as LCD color filters [1,2], molecular wires [3,4], photochromic materials [5,6], organic field-effect transistors (OFETs) [7,8,9,10,11,12], organic light-emitting diodes (OLEDs) [13,14,15,16,17], light-harvesting arrays [18,19]and organic solar cells (OSCs) [20,21,22,23,24,25,26,27,28,29]. PDIs have been utilized as building blocks to construct supramolecular or artificial photosynthetic systems [30,31,32,33]. These organic molecules are advantageous due to their high molar absorptivities, excellent thermal and optical stabilities, reversible redox properties, high photoluminescence quantum yields and self-assembly behaviors [34,35,36,37,38,39,40,41,42,43,44,45,46,47,48].
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