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, ) by Pd-catalyzed Suzuki coupling and a subsequent reductive aromatization reaction in two steps. The PDI-embedded conjugated macrocycl...

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Bibliographic Details
Published in:Organic letters 2023-02, Vol.25 (7), p.1183-1187
Main Authors: Li, Along, Zhang, Xinyu, Wang, Shengda, Wei, Kang, Du, Pingwu
Format: Article
Language:English
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Summary:Herein, we report the facile synthesis and properties of a chiral perylene diimide (PDI)-embedded conjugated macrocycle (cyclo[6]paraphenylene-1,7-perylene diimide, ) 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 was achieved by high-performance liquid chromatography, and their chiral properties were investigated by circular dichroism spectroscopy. The realization of expands the scope of the precise synthesis of PDI-embedded chiral conjugated macrocycles and explores its unique physical properties.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00152