The lithium-sulfur (Li/S) battery is a promising electrochemical storage system due to its high theoretical energy density and cost-effectiveness. However, several challenges hinder its practical applications, including the electronic and ionic insulating nature of both sulfur and the discharge product lithium sulfide (Li 2 S), the formation and shuttling of dissolved lithium polysulfides species between the anode and the cathode, and complicated compositional and structural changes. To address these issues, the scientific community has proposed several strategies, including (i) developing novel cathodes, anodes, binders, and electrolytes; and (ii) advancing the understanding of Li/S redox chemistries. One promising approach involves the confinement of the polysulfides directly via the covalent bonding to the cathode host material. Due to its ability to (i) suppress the polysulfide effect and (ii) reduce the volumetric expansion/contraction during charge/discharge, conjugated organosulfur polymers are notable candidates for high-performance Li/S batteries. Poly(4-(thiophene-3-yl) benzenethiol) (PTBT) is a flexible conjugated organosulfur-based polymer envisioned as a potential candidate to be used as a carbon-additive-free cathode in Li/S batteries. In PTBT, the polythiophene main chain forms a highly conducting framework. In contrast, the benzenethiol side chain facilitates copolymerization with sulfur chains, resulting in the crosslinked organosulfur polymer (S/PTBT). According to our previous study, among the two possible unique structures -HH-TT and HT-HT (H: head, T: tail) -we considered the HT-HT structure because it is predominantly found in the experimental studies, as also supported by the simulation results. The monomeric unit of PTBT, 4-(thiophene-3-yl)benzenethiol (TBT), consists of a benzenethiol group and a thiophene group. These structural features contribute to its electronic properties, as TBT contains a total five π-bonds: two from the thiophene group and three from the benzenethiol group. These π-bonds arise from the unhybridized p-orbitals on each carbon atom, which are parallel to each other and overlap side-by-side. This overlap creates a delocalized π-electron system above and below the plane of the rings. These π-electron systems can interact with the lithium ions from the electrolytes, through the non-bonded cation-π interactions. Recently, it was shown, using a combination of experimental techniques and numerical methods such as molecular dynamics (MD) and density functional theory (DFT) applied to equivalent polymer systems, that cation-π interactions can, in addition to being critical for the diffusion of Li + -ions, enhance the lithium storage property and facilitate lithium ions to stay into the polymer network. However, the cation-π interaction, an ion-induced dipoletype interaction, is not explicitly included in conventional non-polarizable fixed-charge force fields. Therefore, the binding energy of ions to aromatic molecules is usually underestimated in force-field approaches compared to DFT predictions. To overcome this issue, different routes were explored to introduce ion-induced dipole in classical force fields. For instance, Huang et al. employed an empirical approach to calculate cation-π interaction energies in proteins. In that approach, the interaction energy between a cation and a π-bonded molecule is represented by an empirical equation with six free parameters, which depend on two variables: the distance r and the orientation angle θ. Then, the free parameters are optimized based on the benchmark calculations from B3LYP/6-311+G(d,p) theory. In another study, for metal ions, Li et al. proposed to model the ion-induced dipole by enriching the force field functional form with an electrostatic ion-induced dipole -C ij 4 /r 4 ij term, where C ij 4 , which represents the interaction strength, is a fitting parameter for the interactions between specific sites i and j. Such a correction for the ion-induced dipole (ID) interaction leading to a Lennard-Jones plus a correction term (LJ-ID) accurately captures the binding energy obtained from DFT calculations. Following that study, for protein-ligand systems, Turupsu et al. corrected the force field for the cation-π interactions by using the LJ-ID. Differently, for protein-ligand systems, Liu et al. used the nonbonded FIX (NBFIX) feature of the CHARMM force field to capture the cation-π interaction. They selectively optimized the LJ parameters for specific atom pairs, while all other LJ parameters are obtained from standard combining rules. They referenced the quantum mechanical/molecular mechanics (QM/MM) potential energy of mean force data in an aqueous solution to refine the NBFIX parameters.