Dynamically manipulating the handedness of supramolecular chirality and chiroptical properties is a challenging task, which is important in the fabrication of responsive and smart functional materials. Here we report the dynamic evolution of supramolecular chirality inversion and the inversion of corresponding circularly polarized luminescence via the multiple-constituent coassemblies driven by hydrogen bonds. Cyanostilbene-conjugated amino acids were employed as building units, self-assembling into nanoarchitectures with 2₁ column chirality. After being incorporated into a binary coassembly with melamine and its derivative, 2₁ column chirality was transformed into helical chirality with macroscopic nanohelices. Such structural evolution enabled chirality inversion accompanied by inversion of circularly polarized luminescence. Isomerization triggered by photo irradiation appended responsiveness to morphology, supramolecular chirality as well as chiroptical properties, and inversion of circularly polarized luminescence was further achieved specifically. This work illustrating the dynamic chirality evolution and responsiveness provides an alternative perspective for the design and fabrication of smart chiroptical materials.