1,6- and 1,7-regioisomers of dinitro- and diamino-substituted perylene bisimides: synthesis,photophysical and electrochemical properties |
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Authors: | Hsing-Yang Tsai Che-Wei ChangKew-Yu Chen |
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Institution: | Department of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan, ROC |
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Abstract: | 1,6- and 1,7-regioisomers of dinitro- (1,6-3 and 1,7-3) and diamino-substituted perylene bisimides (1,6-1 and 1,7-1) were synthesized. The regioisomers 1,6-3 and 1,7-3 were successfully separated by high performance liquid chromatography and characterized by 500 MHz 1H NMR spectroscopy. Subsequently, the reduction of 1,6-3 and 1,7-3 afforded the corresponding diaminoperylene bisimides 1,6-1 and 1,7-1, respectively. This is the first time 1,6-regioisomers of dinitro- and diamino-substituted perylene bisimides are obtained in pure form. The photophysical and electrochemical properties of 1,6-3 and 1,7-3 were found to be almost the same. However, the regioisomers 1,6-1 and 1,7-1 exhibit significant differences in their optical characteristics. The absorption spectrum of 1,6-1 covers a larger part of the visible region compared to that of 1,7-1. Upon excitation, 1,6-1 also show larger dipole moment change than that of 1,7-1. Time-dependent density functional theory calculations are reported on these dyes in order to rationalize their electronic structure and absorption spectra. |
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Keywords: | 1 6-Dinitroperylene bisimide 1 6-Diaminoperylene bisimide Intramolecular charge transfer Lippert&ndash Mataga equation |
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