Regulating aggregation-induced circularly polarized luminescence of chiral macrocyclic TPEs by tuning the linkage lengths

Wang, Yuxiang; Liao, Qi; Feng, Yabin; Meng, Qi

doi:10.1016/j.molstruc.2024.137695

Journal of Molecular Structure

2024

DOI: 10.1016/j.molstruc.2024.137695

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Regulating aggregation-induced circularly polarized luminescence of chiral macrocyclic TPEs by tuning the linkage lengths

Yuxiang Wang,

Qi Liao,

Yabin Feng

et al.

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Cited by 2 publications

References 65 publications

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Encasing Triaryltriazine with a Bulky Chiral Cap: Luminescent Chiral Crystalline Molecular Rotors with Modulation of Solid-State Chiroptical Properties Mediated by Molecular Rotation

Kim,

Jiang,

Tomita

et al. 2024

J. Am. Chem. Soc.

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A novel structural motif for luminescent chiral crystalline molecular rotors with chiroptical properties correlated with the rotational motion in crystalline media is presented. This scaffold incorporates bulky chiral caps consisting of a homochiral binaphthyl moiety with a triisopropylsilyl (TIPS) group into triaryltriazine, as confirmed by single-crystal X-ray diffraction (XRD) analysis. Variable-temperature solid-state 2 H NMR studies revealed a 4-fold rotation of the phenylenes occurred in the rotor crystal between 263 and 333 K, while a steric rotor analogue shows no rotational motion. Notably, a reduction in the dihedral angle of the binaphthyl moiety upon heating was observed in the chiral rotors, and a corresponding alteration of the circular dichroism (CD) signal was detected in the solid-state, while those of the steric rotors showed no alteration by the temperature change. We propose that the fast rotation of the phenyl rings affects the motion of neighboring isopropyl groups, leading to steric repulsion with the binaphthyl moieties and thereby inducing its conformational change. Furthermore, the chiral rotors exhibited circularly polarized phosphorescence in the solid-state at low temperature, originating from rotational displacement of the phenylene on triphenyltriazine during structural relaxation in the excited state. Meanwhile, the steric rotors showed significant circularly polarized fluorescence induced by the suppressed molecular motion via a sterically hindered lattice environment in the excited state. These results indicate that the bulky chiral cap introduced into the triaryltriazines, acting as a luminescent chiral crystalline molecular rotor, can be a useful scaffold for the modulation of solid-state chiroptical properties via molecular rotational motions.

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Encasing Triaryltriazine with a Bulky Chiral Cap: Luminescent Chiral Crystalline Molecular Rotors with Modulation of Solid-State Chiroptical Properties Mediated by Molecular Rotation

Kim,

Jiang,

Tomita

et al. 2024

J. Am. Chem. Soc.

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Inversion of circularly polarized luminescence by electric current flow during transition

Imayoshi,

Fujio,

Nagaya

et al. 2025

Phys. Chem. Chem. Phys.

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Regulating aggregation-induced circularly polarized luminescence of chiral macrocyclic TPEs by tuning the linkage lengths

Cited by 2 publications

References 65 publications

Encasing Triaryltriazine with a Bulky Chiral Cap: Luminescent Chiral Crystalline Molecular Rotors with Modulation of Solid-State Chiroptical Properties Mediated by Molecular Rotation

Encasing Triaryltriazine with a Bulky Chiral Cap: Luminescent Chiral Crystalline Molecular Rotors with Modulation of Solid-State Chiroptical Properties Mediated by Molecular Rotation

Inversion of circularly polarized luminescence by electric current flow during transition

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