[5]Helicene Based π‐Conjugated Macrocycles with Persistent Figure‐Eight and Möbius Shapes: Efficient Synthesis, Chiral Resolution and Bright Circularly Polarized Luminescence

π‐Conjugated chiral shape‐persistent molecular nanocarbons hold great potential as chiroptical materials, though their synthesis remains a considerable challenge. Here, we present a simple approach using Suzuki coupling of a [5]helicene building block with various aromatic units, enabling the one‐po...

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Veröffentlicht in:Angewandte Chemie 2024-11
Hauptverfasser: Zhou, Qifeng, Yuan, Wei, Li, Yunfei, Han, Yi, Bao, Lintao, Fan, Wei, Jiao, Liuying, Zhao, Yanli, Ni, Yong, Zou, Ya, Yang, Hai‐Bo, Wu, Jishan
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Sprache:eng
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Zusammenfassung:π‐Conjugated chiral shape‐persistent molecular nanocarbons hold great potential as chiroptical materials, though their synthesis remains a considerable challenge. Here, we present a simple approach using Suzuki coupling of a [5]helicene building block with various aromatic units, enabling the one‐pot synthesis of a series of chiral macrocycles with persistent figure‐eight and Möbius shapes. Single‐crystal structures of 7 compounds were solved, and 22 enantiomers were separated by preparative chiral HPLC. A notable pyrene‐bridged figure‐eight macrocycle, with its rigid, fully π‐conjugated and overcrowded structure, exhibited pure excimer emission and outstanding circularly polarized luminescence (CPL) properties, including a large dissymmetric factor (| g lum |=3.8×10 −2 ) and significant CPL brightness ( B CPL =710.5 M −1 cm −1 ). This method provides a versatile synthetic platform for producing various chiral D 2 ‐symmetric figure‐eight macrocycles and singly or triply twisted Möbius macrocycles with C 2 and D 3 symmetry, offering tunable chiroptical properties for CPL applications.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202417749