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Molecules 2014, 19(1), 327-341; doi:10.3390/molecules19010327

1,6- and 1,7-Regioisomers of Asymmetric and Symmetric Perylene Bisimides: Synthesis, Characterization and Optical Properties

Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
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Received: 25 November 2013 / Revised: 10 December 2013 / Accepted: 11 December 2013 / Published: 27 December 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

The 1,6- and 1,7-regioisomers of dinitro- (1,6-A and 1,7-A) and diamino-substituted perylene bisimides (1,6-B and 1,7-B), and 1-amino-6-nitro- and 1-amino-7-nitroperylene bisimides (1,6-C and 1,7-C) were synthesized. The 1,6-A and 1,7-A regioisomers were successfully separated by high performance liquid chromatography and characterized by 500 MHz 1H-NMR spectroscopy, and subsequently, their reduction which afforded the corresponding diaminoperylene bisimides 1,6-B and 1,7-B, respectively. On the other hand, the monoreduction of 1,6-A and 1,7-A, giving the asymmetric 1-amino-6-nitro (1,6-C) and 1-amino-7-nitroperylene bisimides (1,7-C), respectively, can be performed by shortening the reaction time from 6 h to 1 h. This is the first time the asymmetric 1,6-disubstituted perylene bisimide 1,6-C is obtained in pure form. The photophysical properties of 1,6-A and 1,7-A were found to be almost the same. However, the regioisomers 1,6-C and 1,7-C, as well as 1,6-B and 1,7-B, exhibit significant differences in their optical characteristics. Time-dependent density functional theory calculations performed on these dyes are reported in order to rationalize their electronic structure and absorption spectra.
Keywords: 1-amino-6-nitroperylene bisimide; 1-amino-7-nitroperylene bisimide; 1,6-diaminoperylene bisimide; 1,7-diaminoperylene bisimide; asymmetric perylene bisimides; symmetric perylene bisimides 1-amino-6-nitroperylene bisimide; 1-amino-7-nitroperylene bisimide; 1,6-diaminoperylene bisimide; 1,7-diaminoperylene bisimide; asymmetric perylene bisimides; symmetric perylene bisimides
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MDPI and ACS Style

Tsai, H.-Y.; Chang, C.-W.; Chen, K.-Y. 1,6- and 1,7-Regioisomers of Asymmetric and Symmetric Perylene Bisimides: Synthesis, Characterization and Optical Properties. Molecules 2014, 19, 327-341.

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