Next Article in Journal
Development of a Supercritical Fluid Chromatography-Tandem Mass Spectrometry Method for the Determination of Azacitidine in Rat Plasma and Its Application to a Bioavailability Study
Previous Article in Journal
Cytoprotective Effect of American Ginseng in a Rat Ethanol Gastric Ulcer Model
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

,
 and
*
Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan
* Author to whom correspondence should be addressed.
Received: 25 November 2013 / Revised: 10 December 2013 / Accepted: 11 December 2013 / Published: 27 December 2013
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1661 KB, uploaded 18 June 2014]   |  

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 (CC BY 3.0).

Supplementary material

SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert