The generation of initial structures for PDI-diMMAx, PDI-diStx, PDI-tetraMMAx, PDI-tetraStx, and PDI-poly(St36-co-VPy4) was achieved utilizing custom scripts based on the Open Babel toolbox. The geometry of the oligomer with DP=x was obtained by iteratively linking the corresponding monomer moieties to randomly-selected conformers from preceding generation (x-2 for PDI-diMMAx, PDI-diStx, and x-4 for PDI-tetraMMAx, PDI-tetraStx). Investigations into the folding behavior of PDI-diMMAx, PDI-diStx, PDI-tetraMMAx, PDI-tetraStx, and PDI-poly(St36-co-VPy4) in DMF/H2O (5/95, v/v) solution were performed using the same setup as for PDI-tetraSt8, and PDI-tetraMMA8. The spatial distribution of atoms perpendicular to the PDI plane was calculated for each frame within the production stage of the MD simulation. We consider a PDI oligomer to be encapsulated if more than 15 non-hydrogen atoms (C, N, O, Br) were located within a range of 1.5 nm to 6.5 nm from each side of the PDI core's plane origin. To simulate the aggregation behavior of PDI-poly(St36co-VPy4), the initial structures were constructed by packing the equilibrated snapshots from 8 different configurations in a simulation box of 120 × 120 × 120 Å 3 and solvated with DMF/H2O (5/95, v/v), and simulated using the same MD setup as PDI-tetraSt8 and PDI-tetraMMA8 aggregates.