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Materials 2014, 7(8), 5488-5506; doi:10.3390/ma7085488

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Received: 14 June 2014 / Revised: 18 July 2014 / Accepted: 23 July 2014 / Published: 25 July 2014
(This article belongs to the Special Issue Advances in Colorants 2014)
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Abstract

Three asymmetric amino-substituted perylene bisimide dyes with different n-alkyl chain lengths (n = 6, 12, or 18), 1-(N,N-dialkylamino)perylene bisimides (1a1c), were synthesized under mild condition in high yields and were characterized by 1H NMR, 13C NMR (nuclear magnetic resonance), HRMS (High Resolution Mass Spectrometer), UV-Vis and fluorescence spectra, as well as cyclic voltammetry (CV). These molecules show intense green color in both solution and solid state and are highly soluble in dichloromethane and even in nonpolar solvents, such as hexane. The shapes of the absorption spectra of 1a1c in solid state and in solution were found to be virtually the same, indicating that the long alkyl chains could efficiently prevent aggregation. They exhibit a unique charge transfer emission in the near-infrared region, of which the peak wavelengths show strong solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1-aminoperylene bisimide (2). Furthermore, all of the compounds exhibit two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory (DFT) calculations performed on these dyes are reported in order to rationalize their molecular structures and electronic properties. View Full-Text
Keywords: green dyes; 1-(N,N-dialkylamino)perylene bisimides; intramolecular charge transfer; solvatochromism; Lippert-Mataga equation; density functional theory calculations green dyes; 1-(N,N-dialkylamino)perylene bisimides; intramolecular charge transfer; solvatochromism; Lippert-Mataga equation; density functional theory calculations
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MDPI and ACS Style

Chang, C.-W.; Tsai, H.-Y.; Chen, K.-Y. Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties. Materials 2014, 7, 5488-5506.

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