Facile synthesis and replacement reactions of mono-substituted perylene bisimide dyes

Mono-substituted perylene bisimides were synthesized in high yields under mild condition. The starting material was mono-nitrified perylene bisimides instead of usual perylene bisimides halogenated at different levels. Besides phenols and amine, the nucleophilic reagents included alcohol and thiol. The substitution of nitro group was easier and more effective than the substitution of halogen atoms. But the substitution reaction of pyrrolidine afforded mono- and 1,6-disubstituted perylene bisimides owing to the high activity of nitrified perylene bisimides and pyrrolidine. Several replacement reactions between phenols and alcohol based on phenol mono-substituted perylene bisimide were also found. The replacement reactions between phenols was fast and in high yield. The absorption of the mono-substituted perylene bisimides were tunable in the whole visible region.

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► Substitution reactions of mono-nitrified perylene bisimides were investigated.
► Substitution groups including phenols, alcohol, thioalcohol and amine.
► Substitution reactions carried out at room temperature or fluxed chloroform.
► Replacement reactions of mono-phenol substituted PBIs were found.