Circularly polarized luminescence (CPL) is an emerging field with significant applications in molecular electronics, optical materials, and chiroptical sensing. Achieving efficient CPL emission in organic systems remains a major challenge, particularly in the development of materials with high fluorescence quantum yields (ΦF) and large luminescence dissymmetry factors (glum). Herein, we report the efficient synthesis of shape-persistent tetraphenylethylene macrocycles and investigate its potential as a CPL material. Chiral side chains were introduced to induce chiroptical properties. The macrocycles and their properties were characterized using NMR, MALDI-TOF MS, FT-IR, TGA, DSC, UV-Vis spectroscopy, SEM, fluorescence spectroscopy, ECD, and CPL. A significant fluorescence enhancement was observed upon aggregation, demonstrating a typical aggregation-induced emission (AIE) behavior. Moreover, one of the macrocycles in the solid state displayed distinct CPL emission with a high glum of 2 × 10−2 and a ΦF value reaching 60%, and exhibited aggregation-induced circularly polarized luminescence (AICPL). These findings highlight the advantage of using a macrocycle with a noncollapsible backbone for the design of organic systems with CPL property, offering promising applications in chiroptical materials.
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