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• Three pairs of chiral binaphthyl based macrocyclic tetraphenylethylenes (TPEs) with flexible macrocycle backbones and different linkage lengths were designed and synthesized. • The homochiral helical orientations of TPEs in the crystal structures demonstrate the successful chirality transfer from chiral binaphthyl to TPE via the soft macrocycle backbone. • Obvious aggregation-induced emission (AIE) and CPL properties can be detected owing to the chiral macrocyclic architectures. • The chiral macrocycle with the longest linkage length can produce the largest aggregation-induced circularly polarized luminescence (AI-CPL) signals in films with luminescence dissymmetry factor (g lum) up to 1.9 × 10−3. Developing chiral macrocycles with intense circularly polarized luminescence (CPL) has received considerable interest. The chirality transfer in the chiral macrocycles with separated chiral sources and luminophores is crucial but rarely explored. In this paper, we designed and synthesized three pairs of chiral binaphthyl based macrocyclic tetraphenylethylenes (TPEs) with flexible macrocycle backbones and different linkage lengths. The homochiral helical orientations of TPEs in the crystal structures demonstrate the successful chirality transfer from chiral binaphthyl to TPE via the soft macrocycle backbone. Obvious aggregation-induced emission (AIE) and CPL properties can be detected owing to the chiral macrocyclic architectures. Most importantly, the chiral macrocycle with the longest linkage length can produce the largest aggregation-induced circularly polarized luminescence (AI-CPL) signals in films with luminescence dissymmetry factor (g lum) up to 1.9 × 10−3. [Display omitted] [ABSTRACT FROM AUTHOR]