Fluorescent J-Aggregates

Significance

The authors report a highly fluorescent J-aggregate assembled from the highly stable fluorophore perylene bisimide. The unprecedented packing of perylene bisimide dyes in a strongly slipped arrangement was tailored by twisting of the perylene core enforced by bay substituents, the attachment of trialkoxyphenyl ­wedges, and head-to-tail alignment of the dyes through hydrogen-bonding interactions. Cleavage of the methyl ether groups in the bay substituents and the N-benzyl groups in the imide positions with BBr₃ in anhydrous dichloromethane provided the deprotected perylene bisimide intermediate. Subsequent esterification with 3,4,5-tridodecyloxybenzoic acid afforded the target dye.