<b>Self-Similar Chiral Organic Molecular Cages</b>

The endeavor to enhance utility of organic molecular cages involves the evolution of them into higher-level chiral superstructures with self-similar, presenting a meaningful yet challenging. In this work, 2D tri-bladed propeller-shaped triphenylbenzene serves as building blocks to synthesize a racemic 3D tri-bladed propeller-shaped helical molecular cage. This cage, in turn, acts as a building block for a pair of higher-level 3D tri-bladed chiral helical molecular cages, featuring multilayer sandwich structures and displaying elegant characteristics with self-similarity in discrete superstructures at different levels. The evolutionary procession of higher-level cages reveals intramolecular self-shielding effects and exclusive chiral narcissistic self-sorting behaviors. Enantiomers higher-level cages can be interconverted by introducing an excess of corresponding chiral cyclohexanediamine. In the solid state, higher-level cages self-assemble into supramolecular architectures of <i>L</i>-helical or <i>D</i>-helical nanofibers, achieving the scale transformation of chiral characteristics from chiral atoms to microscopic and then to mesoscopic levels.