Work

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

Year: 2025

Type: article

Abstract: 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. Achieving molecular chirality with enantiostability in π-conjugated foldamers is challenging due to weak π-π interactions and easy racemization. Here, the authors employ a 3D π–π stacking strategy within a 1,8-diarylnaphthalene framework, achieving exceptional configurational stability and tunable optical properties.

Source: Communications Chemistry

DOI: 10.1038/s42004-025-01855-x