New derivates of 1,6,7,12-tetra-chloroperylene-9,10-di-carboxylic di-n-butyl mono-imide di-n-butylester
J.S. van Mullem (TU Delft - Applied Sciences)
W.F. Jager – Mentor (TU Delft - ChemE/Advanced Soft Matter)
Ernst J. R. Sudhölter – Graduation committee member (TU Delft - ChemE/Advanced Soft Matter)
Rienk Eelkema – Graduation committee member (TU Delft - ChemE/Advanced Soft Matter)
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Abstract
Synthesis of new perylene-3,4,9,10-tetra-carboxylic acid (PTCA) derivates is a research topic that has rapidly developed during the last decades. Current synthetic efforts are largely focussed on functionalizing the perylene core, via either bay- or ortho-substitution. The aim of this research project was to synthesize novel perylene mono-imide di-ester derivates by attaching different substituents at the bay-positions. The first synthetic route that was attempted in this research project was a route via a perylene mono-anhydride mono-imide derivate. The anhydride was attached to this molecule to activate the relevant bay-positions. It was found that the anhydride is not stable enough to withstand the reaction conditions that were used in an attempt to substitute the relevant bay positions. The next synthetic route that was attempted in this research project was a route via a perylene di-ester mono-imide derivate. Reactions were performed to explore whether the di-ester was able to activate the relevant bay-positions. It was found that at the used reaction conditions, phenol exchange takes place on the bay-positions of the perylene core. Due to the challenges that arose, the target compounds of this project have not been synthesized. However, three other new PTCA derivates have been synthesized during this project.