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

Content Provider	PubMed Central
Author	Chen, Kew-yu Chang, Che-wei
Editor	Kevill, Dennis N.
Copyright Year	2014
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.
Related Links	http://dx.doi.org/10.3390/ijms151222642
Ending Page	22660
Page Count	19
Starting Page	22642
File Format	PDF
ISSN	14220067
e-ISSN	14220067
Journal	International Journal of Molecular Sciences
Issue Number	12
Volume Number	15
Language	English
Publisher	MDPI
Publisher Date	2014-12-01
Access Restriction	Open
Rights Holder	MDPI
Subject Keyword	Physical and Theoretical Chemistry Inorganic Chemistry Organic Chemistry Spectroscopy Molecular Biology Catalysis Computer Science Applications Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Spectroscopy Organic Chemistry Medicine Molecular Biology Physical and Theoretical Chemistry Catalysis Inorganic Chemistry Computer Science Applications

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