Abstract: The synthetic chiral polysilane adopts a rigid rod-like spiral structure, which has unique circular dichroism (CD) characteristics in near ultraviolet (UV) region and can be easily decomposed by UV irradiation. Therefore, chiral polysilanes have become excellent chiral scaffolds for inducing supramolecular chiral assembly of achiral polymers in recent years. In order to further verify the chiral scaffolding capability of chiral polysilane and enrich the types of achiral or optically inactive polymers that were induced to perform supramolecular chiral assembly, hyperbranched polyfluorenes (HPF8s) with different branching units were synthesized on the basis of Suzuki polycondensation reaction, which laid a foundation for further realization of chiral supramolecular assembly of hyperbranched main-chain conjugated polymers induced by using chiral polysilanes as the chiral scaffolds. The supramolecular chiral assembly of HPF8s was successfully induced by an enantiomeric pair of rigid rod-like helical polysilanes bearing (S)- and (R)-2-methylbutyl groups (PSi-S(R)) in a binary solvent mixtures of chloroform and methanol. Optimizing experimental conditions were crucial for boosting the CD amplitudes of HPF8/PSi-S and HPF8/PSi-R hetero-aggregates. The effects of various conditions on the supramolecular chiral assembly behavior of hyperbranched polyfluorenes induced by chiral polysilanes were systematically investigated. Results showed that the choice of cosolvent, the volume ratio of good and poor solvent, the mass concentration ratio of HPF8s to PSi-S(R), and the branching unit content of HPF8s presented great impacts on the chiral expression of the hetero-aggregates. In addition, the optically active HPF8s homo-aggregates were produced by complete photoscissoring reactions at 313 nm, which could be assigned to the Siσ-Siσ* transitions of PSi-S and PSi-R.