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<p>Achieving molecular chirality with enantiostability in purely π-conjugated foldamers remains a substantial challenge due to inherently weak π-π stacking interactions and facile racemization. Herein, we introduce a novel design strategy employing synergistic intramolecular 3D π–π stacking networks within a 1,8-diarylnaphthalene framework, enabling foldamers to exhibit extraordinary configurational stability. A systematic series of quinoxaline- and phenazine-based foldamers incorporating carbazole (CZ) and diphenylamine (DPA) donors were synthesized, with chiral configurations stabilized through complementary face-to-face and laterally offset π–π stacking interactions. Single-crystal X-ray analyses and computational studies confirmed the formation of complex intramolecular π-networks, providing exceptional racemization barriers (Δ<i>G</i><sup>‡</sup> up to 26.06 kcal mol<sup>-1</sup>), exceeding conventional atropisomers. Additionally, the modular donor-acceptor design facilitates full-color circularly polarized luminescence (469–684 nm), maintaining high dissymmetry factors (|<i>g</i><sub>lum</sub> | &gt; 10<sup>-3</sup>) across solution and solid-state environments. This work establishes a generalizable principle for constructing chiral foldamers with enantiostability and tunable optical properties through tailored 3D aromatic interactions, offering significant advances in chiral optoelectronics and responsive materials.</p><p></p>

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Synergistic 3D π–π networks enforce persistent foldamer configuration with tunable full-color circularly polarized luminescence

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年12月26日

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  • Hao Hu,
  • Qiangsheng Zhang,
  • Ziyan Wu,
  • Hongtao Liu,
  • Jialin Xie,
  • Zhenchang Wen,
  • Weijie Chi,
  • Jianwei Li,
  • Chunman Jia

摘要

Achieving molecular chirality with enantiostability in purely π-conjugated foldamers remains a substantial challenge due to inherently weak π-π stacking interactions and facile racemization. Herein, we introduce a novel design strategy employing synergistic intramolecular 3D π–π stacking networks within a 1,8-diarylnaphthalene framework, enabling foldamers to exhibit extraordinary configurational stability. A systematic series of quinoxaline- and phenazine-based foldamers incorporating carbazole (CZ) and diphenylamine (DPA) donors were synthesized, with chiral configurations stabilized through complementary face-to-face and laterally offset π–π stacking interactions. Single-crystal X-ray analyses and computational studies confirmed the formation of complex intramolecular π-networks, providing exceptional racemization barriers (ΔG‡ up to 26.06 kcal mol-1), exceeding conventional atropisomers. Additionally, the modular donor-acceptor design facilitates full-color circularly polarized luminescence (469–684 nm), maintaining high dissymmetry factors (|glum | > 10-3) across solution and solid-state environments. This work establishes a generalizable principle for constructing chiral foldamers with enantiostability and tunable optical properties through tailored 3D aromatic interactions, offering significant advances in chiral optoelectronics and responsive materials.