A novel boron-stereogenic fluorophore with dual-state circular polarization luminescence via a self-dispersing strategy†

Abstract

Molecular engineering is a reliable approach for the development of circularly polarized luminescence (CPL) materials for various applications. However, creating dual-state CPL platforms that possess chirality while achieving a delicate balance between molecular rigidity and flexibility remains a formidable challenge. In this study, a novel bisarylboron-anchored pyrrolylsalicylhydrazone (BOPSH) platform was synthesized via a facile “one-pot” condensation. These key aryl-boron substituents not only provide structural rigidity to the fluorophore, enhancing the bright emission and suppressing emission quenching from π–π stacking in solid states due to their twisting and bulky steric effects, but also generate a boron-stereogenic center and enable strong CPL by promoting intramolecular charge-transfer transitions. As a result, these BOPSHs show intense absorption and strong dual-state emissions in both solution and solid states (with Φ_PL value approaching unity), emitting across the visible region with excellent chemical, photostability, and thermal stability. Meanwhile, their enantiomers display dual-state CPL performance, with luminescence dissymmetry factors (g_lum) up to 9.40 × 10⁻³, and CP electroluminescence (EL) with a dissymmetry factor (g_EL) of 3.07 × 10⁻³, along with excellent maximum external quantum efficiencies (η_ext,max) of 5.0%, approaching the theoretical limit for fluorescent molecules. We expect our study to break new ground in the construction of chiral dual-state materials with diverse structures.