This work provides the finding of aggregation-induced circular dichroism (AICD), optical properties and helical assemblies of π–π conjugated molecule hexaphenylsilole (HPS). As an achiral molecule, HPS was found to exhibit unusual AICD and circular polarized luminescence (CPL). Upon aggregation, it self-assembled into fluorescent helical nanofiber and nanotubes. Theoretical modeling suggests that van der Waals interaction between HPS monomers plays an essential role in the formation of helical nanofibers. These kinds of molecules have important applications given the increasing demand of miniaturized optics and electronic devices.