The dynamic transfer of a conjugated polymer's organization-dependent properties from the solution state to the solid film state was probed by circularly polarized luminescence (CPL) and circular dichroism (CD) spectroscopy. Different supramolecular organizations within films and aggregate solutions of a chiral poly(p-phenylenevinylene) derivative led to opposite CPL and CD spectra. These dramatic property differences were controlled by regulating the polymer's self-assembly through solvent selection and film annealing. Therefore, different processing conditions can greatly affect the functional properties of conjugated polymer films employed in various optoelectronic applications.