One-Step Synthesis of a Pyrene Dimer with Intense Excimer Circularly Polarized Luminescence
Qing-Yu Meng , Xiao-Fang Hou , Jia-Qi Zhao , Jun-Qing Luo , Wen-Kai Chen , Zhimin Sun , Jiao-Mei Cheng , Xu-Man Chen , He-Lue Sun
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (20) : 2655 -2660.
One-Step Synthesis of a Pyrene Dimer with Intense Excimer Circularly Polarized Luminescence
The development of circularly polarized luminescence (CPL) materials from simple organic molecules is of critical importance for advancing their practical applications, yet it remains hindered by challenges such as low dissymmetry factors (glum) and complex synthetic process. Herein, we report a facile one-step [2+2] condensation strategy to access a Schiff-base pyrene dimer featuring 1,6-substituted pyrenes and trans-1,2-diaminocyclohexane units in 77% yield. Taking advantages of face-to-face π-π stacking of pyrene rings in the constrained D2 symmetric structure, intense excimer CPL was successfully realized with a |glum| value of 0.021 and a CPL brightness, BCPL, value of 154.5 M-1·cm-1. The optimized excited state structures reveal that the high |glum| value arises from the parallel arrangement of electric and magnetic dipole transition moments. Importantly, the rigid pyrene dimer architecture ensures robust CPL performance invariant under diverse conditions, including changes in temperature, concentration, and solvents, as well as in polymer films.
Circularly polarized luminescence / Pyrene dimer / Pyrene excimer / One-step synthesis / Chiral macrocycle
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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