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Materials 2014, 7(11), 7548-7565; doi:10.3390/ma7117548

1,7-Bis-(N,N-dialkylamino)perylene Bisimides: Facile Synthesis and Characterization as Near-Infrared Fluorescent Dyes

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Received: 20 October 2014 / Revised: 10 November 2014 / Accepted: 13 November 2014 / Published: 24 November 2014
(This article belongs to the Special Issue Luminescent Materials and Devices)
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Abstract

Three symmetric alkylamino-substituted perylene bisimides with different n-alkyl chain lengths (n = 6, 12, or 18), 1,7-bis-(N,N-dialkylamino)perylene bisimides (1a1c), were synthesized under mild condition 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). These compounds show deep 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 the solution and solid state were found to be almost the same, indicating that the long alkyl chains could efficiently prevent intermolecular contact and aggregation. They show a unique charge transfer emission in the near-infrared region, of which the peak wavelengths exhibit strong solvatochromism. The dipole moments of the molecules have been estimated using the Lippert–Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1,7-diaminoperylene bisimide (2). Moreover, all the dyes exhibit two irreversible 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 rationalize their electronic structure and optical properties. View Full-Text
Keywords: near-infrared fluorescent dyes; 1,7-bis-(N,N-dialkylamino)perylene bisimides; intramolecular charge transfer; solvatochromism; Lippert–Mataga equation; density functional theory calculations near-infrared fluorescent dyes; 1,7-bis-(N,N-dialkylamino)perylene bisimides; intramolecular charge transfer; 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. 1,7-Bis-(N,N-dialkylamino)perylene Bisimides: Facile Synthesis and Characterization as Near-Infrared Fluorescent Dyes. Materials 2014, 7, 7548-7565.

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