The hierarchical organization strategy has realized elaborate supramolecular structures that are difficult to achieve by a one-pot thermodynamically driven self-assembly. Self-assembly via Schiff base formation of the preorganized tripodal helical unit 2(2+), which is composed of the tris(bipyridyl) ligand 1 and octahedral metal ion (RuII and FeII), lead to two supramolecular structures, i.e., a macrobicyclic dimer and an interlocked helicate. Notably, the interlocked helicate had a unique motif with an elongated shape (similar to 58 angstrom) and linearly aligned metal centers with homochiral configurations (all-Delta or all-Lambda), which shows potential for allosteric regulation based on the long-range transmittance of the structural information.