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

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

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Received: 25 November 2013; in revised form: 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
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.

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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.

AMA 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(1):327-341.

Chicago/Turabian Style

Tsai, Hsing-Yang; Chang, Che-Wei; Chen, Kew-Yu. 2014. "1,6- and 1,7-Regioisomers of Asymmetric and Symmetric Perylene Bisimides: Synthesis, Characterization and Optical Properties." Molecules 19, no. 1: 327-341.


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