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

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Abstract 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 (|glum|=3.8×10−2) and significant CPL brightness (BCPL=710.5 M−1cm−1). This method provides a versatile synthetic platform for producing various chiral D2‐symmetric figure‐eight macrocycles and singly or triply twisted Möbius macrocycles with C2 and D3 symmetry, offering tunable chiroptical properties for CPL applications.

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