This study reports the synthesis and characterization of enantiopure higher-level triphenylbenzene (TPB)-based molecular cages, 4P-HTMC and 4M-HTMC, using dynamic covalent chemistry (DCC). The TPB-based [2+3] O-bridged oxacalixarene molecular cage (TMC) serves as a 3D tri-bladed propeller-shaped building block. The resulting higher-level molecular cages exhibit elegant 3D tri-bladed helical structures with hetero-pores (3.9 and 9.8 Å) and display self-similarity across different levels. The cages demonstrate exclusive chiral narcissistic self-sorting behaviors, where only one chiral form is selectively formed. The enantiomers can be interconverted by introducing excess chiral cyclohexanediamine. In the solid state, the cages self-assemble into supramolecular architectures of L-helical or D-helical nanofibers, achieving scale transformation of chiral characteristics from chiral atoms to microscopic and mesoscopic levels. The study highlights the potential of organic molecular cages (OMCs) in applications such as separation, catalysis, and recognition. The research also addresses the challenges in constructing OMC-based superstructures with enhanced properties and explores the self-sorting and self-assembly behaviors of OMCs. The findings provide insights into the design and synthesis of OMC-based higher-level supramolecular architectures for improved applications.This study reports the synthesis and characterization of enantiopure higher-level triphenylbenzene (TPB)-based molecular cages, 4P-HTMC and 4M-HTMC, using dynamic covalent chemistry (DCC). The TPB-based [2+3] O-bridged oxacalixarene molecular cage (TMC) serves as a 3D tri-bladed propeller-shaped building block. The resulting higher-level molecular cages exhibit elegant 3D tri-bladed helical structures with hetero-pores (3.9 and 9.8 Å) and display self-similarity across different levels. The cages demonstrate exclusive chiral narcissistic self-sorting behaviors, where only one chiral form is selectively formed. The enantiomers can be interconverted by introducing excess chiral cyclohexanediamine. In the solid state, the cages self-assemble into supramolecular architectures of L-helical or D-helical nanofibers, achieving scale transformation of chiral characteristics from chiral atoms to microscopic and mesoscopic levels. The study highlights the potential of organic molecular cages (OMCs) in applications such as separation, catalysis, and recognition. The research also addresses the challenges in constructing OMC-based superstructures with enhanced properties and explores the self-sorting and self-assembly behaviors of OMCs. The findings provide insights into the design and synthesis of OMC-based higher-level supramolecular architectures for improved applications.