Perylene dyes represent a class of inherently robust and outstandingly versatile organic compounds that have been extensively utilized for a wide range of high technology applications; including organic field effect transistors and light emitting diodes, organic solar cells, optical switches etc.[1−2] Simultaneously, these dyes have also been utilized in the synthesis of a wide range of molecular dyads and more complex systems, that absorb visible light and undergo directional photoinduced energy/electron transfer.[3−5]
Herein, we want to present our recent work which includes a highly efficient, scalable, and robust synthesis of various novel 1,7-dibromo- and 1,6,7,12-tetrachloro-functionalized perylene derivatives from commericially available perylene-3,4,9,10-tetracarboxylic bisanhydride.[6−7] These derivatives are valuable and versatile synthon as they possess at least one anhydride functionality in addition to the 1,7-dibromo- and 1,6,7,12-tetrachloro-substituents. It allows for a virtually limitless attachment of susbstituents both at peri and the bay positions. Finally, the synthesized derivatives are applied for the construction of visible-light-induced hydrogen evolution systems based on dye–catalyst assemblies.
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[7] Sengupta, S.; Dubey, R. K.; Hoek, R. W. M.; van Eeden, S. P. P.; Gunbaş,
D. D.; Grozema, F. C.; Sudhölter, E. J. R.; Jager W. F. J. Org. Chem. 2014, 79, 6655–6662.