Dual-Stimuli-Responsive Turn-On Luminescence of Chiral Bisimidazolyl BINOL Dimethyl Ether Crystals

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  • Murata, Honami
    Department of Chemistry and Life Science, Graduate School of Engineering Science, Yokohama National University
  • Suzuki, Seika
    Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University
  • Terakubo, Kazuki
    Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University
  • Imai, Yoshitane
    Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University
  • Ito, Suguru
    Department of Chemistry and Life Science, Graduate School of Engineering Science, Yokohama National University

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Stimuli-responsive organic luminescent crystals have attracted significant attention in recent years for their potential in sensor and memory applications. While turn-on luminescence is superior in detection sensitivity compared with turn-off luminescence, the development of organic crystals that exhibit turn-on luminescence in response to multiple stimuli remains a significant challenge. Herein, the crystals of chiral bisimidazolyl 1,1′-bi-2-naphthol (BINOL) dimethyl ether have exhibited a dual-stimuli-responsive turn-on luminescence based on two distinct mechanisms. In the crystalline state, luminescence was substantially quenched by the intermolecular hydrogen bonds between the imidazole rings. Mechanical stimulation induced a transition to a blue-violet-emissive amorphous state. In contrast, thermal stimulation produced an orange luminescence, attributed to excited-state intramolecular proton transfer (ESIPT) luminescence from thermally demethylated products. Furthermore, the thermally induced state exhibited circularly polarized luminescence (CPL), marking a rare instance of stimuli-responsive turn-on CPL in a solid-state system. This study provides new insights into environmental and structural factors for solid-state luminescent properties and advances the design guidelines for multifunctional luminescent sensors.

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