Concerning the conformation of [8]CPP, the dihedral angle formed between two connected phenyl rings, using the torsional parameters from Ref. [53], is predicted to be 31.6°compared with the value of 30.8°at the B3LYP/6-31G* level. The dihedral angle for the linear oligomers is around 40°, with smaller values here due to the cyclic topology. We can thus conclude that the tailored FF is able to also reasonable reproduce the geometrical shape of single [8]CPP molecules, and thus intra-and inter-molecular structural features relevant for the aggregation process. teractions. In curve 2d, the molecule at that particular relative orientation, is rotated to explore the roughness of the graphite surface, which could play an important role in the 2D translational diffusion of these molecules. Small differences between HF-3c and FF energies are found in the vicinity of the minimum, with the main ones being located at distances shorter than the minimum, where the repulsive part of the potential is predominant. The mean average error for all the curves is 1.80 kcal/mol, and it is largely originated from the fitting of the rotational profile in the curve 2d, for which the agreement is not quantitative (for instance HF-3c predicts a barrier of 3.4 kcal/mol and the FF of 2.6 kcal/mol). Despite that, the elsewhere small error between the HF-3c curves and the FF demonstrate that the force field can reasonably describe the energetics of aggregation and adsorption on graphite.