Synthesis and Physical Properties of a Perylene Diimide-Embedded Chiral Conjugated Macrocycle.

Herein, we report the facile synthesis and properties of a chiral perylene diimide (PDI)-embedded conjugated macrocycle (cyclo[6]paraphenylene-1,7-perylene diimide, [6]CPP-PDI 1,7 ) by Pd-catalyzed Suzuki coupling and a subsequent reductive aromatization reaction in two steps. The PDI-embedded conjugated macrocycle showed a significant redshift (>110 nm for absorption) compared to the PDI molecule. Moreover, efficient resolution of chiral enantiomers with ( P )/( M )-[6]CPP-PDI 1,7 was achieved by high-performance liquid chromatography, and their chiral properties were investigated by circular dichroism spectroscopy. The realization of [6]CPP-PDI 1,7 expands the scope of the precise synthesis of PDI-embedded chiral conjugated macrocycles and explores its unique physical properties.