Abstract: The chirality of amino acid containing aggregation induced emission molecule silole (SI) has successfully transferred from the pendant to the silole scaffold. Chirality of the amino acid attachments can not only induce helical conformation of the molecules, but also be amplified as helical assemblies on the higher order architectures of the molecules. The self-assemblies were determined by both the chemical structures of the molecules and the surfaces/interfaces of the molecules. With the employment of atomic force microscope and Langmuir-Blodget technique, the self-assembly of the molecules on the surface of mica and on the air/water interface upon the evaporation of the solvent toluene was studied, respectively. The molecules self-assembled into helical fibers, while self-assembled into aligned ridges on the air/water interface at lower surface pressure, and with aligned nanofibers absorbed on the film at high surface pressure. In toluene the molecules formed intermolecular hydrogen bonds, which stabilized helical assemblies. The hydrogen bonds were patterned in a dislocation way due to the propeller shape of the molecules and the chirality of the amino acid attachments. On the air/water interface hydrogen patterns failed to form due to the lateral affinity between the amino acid attachments and water, and the hydrophobic repulsion between silole scaffold and water. Film of aligned ridges was formed with aligned fibers attaching to the surface of the aligned ridges. The aligned fibers had the same orientation with the underlying substrate mica, suggesting that the surface also played a critical role in determining the morphology of the assemblies.