Novel derivatives of 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic acid

Synthesis, electrochemical and optical properties

Journal article (2016)

Authors

R. Dubey ChemE/Opto-electronic Materials - AS
N. Westerveld ChemE/O&O groep - AS
Ernst J. R. Sudhölter OLD ChemE/Organic Materials and Interfaces
F.C. Grozema ChemE/Opto-electronic Materials - AS
W.F. Jager OLD ChemE/Organic Materials and Interfaces
Research Group
OLD ChemE/Organic Materials and Interfaces
Copyright: © 2016 R. Dubey, N. Westerveld, Ernst J. R. Sudhölter, F.C. Grozema, W.F. Jager
DOI
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https://doi.org/10.1039/c6qo00374e
More Info
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Published Date

01-11-2016

Language

English

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Research Group

OLD ChemE/Organic Materials and Interfaces

Abstract

A family of novel unsymmetrical "peri"-substituted perylene-3,4,9,10-tetracarboxylic acid derivatives (5-10), with 1,6,7,12-tetrachloro-substituents at the bay-positions, has been synthesized. Subsequently, their redox and optical properties have been explored with the intent of unveiling opto-electronic characteristics of these newly synthesized compounds. To synthesize these new compounds, pure 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic tetra-n-butylester (4) has been employed as the precursor and the structural modifications have been carried out exclusively at the "peri" positions in an efficient manner. The two synthons prepared in this work, 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic di-n-butylester monoanhydride (5) and 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic monoimide monoanhydride (8), are extremely valuable and versatile starting materials as they possess free anhydride functionality at the "peri" position in addition to the 1,6,7,12-tetrachloro-bay-substituents. Finally, the conventional methodology for the synthesis of 1,6,7,12-tetraphenoxy-bay-functionalized perylene bisimides and perylene bisbenzimidazoles has been modified to make it faster and more convenient.