We had demonstrated a modular synthetic approach toward chiral π-conjugated macrocyclic luminogens (RBT and SBT) integrating axis and helical chirality, whereas the chiral configuration was evidently confirmed by crystal analysis. After Yamamoto polymerization of the chiral macrocycles, a pair of chiral luminescent porous organic polymers with hierarchical porous structure was readily obtained and characterized. Owing to the existence of tetraarylethene units in the macrocycles, the CCMs all displayed aggregation-induced emission property and high emission efficiency in the solid state. These chiral small molecules and POPs also displayed mirror-imaged CD and CPL signals in solution, as nano-aggregates or suspension in MeOH, whereas the luminescence dissymmetry factor |g lum | was on the order of 10 -3 . Via energy transfer and chirality transfer from chiral POPs as host to guest dyes, the mixing of chiral POPs and Rhodamins had feasibly yielded CPL-active composites with tunable emission colors. These hierarchical chiral POPs were further utilized as fluorescence sensors for explosive molecules and chiral nitro-aromatics, which showed satisfactory enantioseletivity. These chiral conjugated macrocycles have established a modular approach toward chiral AIEgens, and the presented chiral macrocyclic POPs are the first two examples of conjugated POPs based on AIEgens with defined helicity. This work will promote the design and synthesis of more chiral porous polymers and