Chirality transfer and amplification are prevailing in biological systems, which play vital roles in the homochirality of life. Systems with remote chirality transfer and amplification remain actively pursued, aiming to construct novel chiral materials for advanced applications. Chiral supramolecular assembly stands out as a promising way to construct molecular assemblies through multiple synergistic noncovalent interactions, which enable the construction of various chiral materials. Here, we have developed a novel chiral monomer that was able to self-assemble in nonpolar solvents and afforded chiral fibers. The self-assembly process was found to be tuned by solvent composition and concentration. The self-assembly kinetics were affected by solvents and concentrations as well. The chirality can be transferred from the remote chiral center at the peripheries of the compound to the center of the molecule and was amplified during the self-assembly process via helical stacking of the adjacent monomers. Furthermore, CPL and energy transfer relay systems were also successfully realized with the chiral self-assemblies.