Conjugated organic oligomers are central to the development of efficient organic electronic devices and organic photovoltaics. However, the torsional flexibility of many of these organic materials, in particular oligothiophenes, can adversely affect charge transfer properties. Although previous studies have examined the torsional flexibility of oligothiophenes, there have been only limited studies of the effects of 200 210 interchain interactions on their torsional potentials. B97-D/TZV(2d,2p) was first benchmarked against a CCSD(T)/aug-cc-pVTZ torsional potential for bithiophene as well as SCS-MP2/TZVPP interaction energies for noncovalent sexithiophene (6T) dimers. The effect of neighboring chains on three distinct torsional modes of sexithiophene was studied using B97-D. Complexation with one or more neighboring chains has a dramatic effect on each of these torsional potentials. For example, for two stacked chains, alternated twisting motions are competitive with torsion about a single terminal dihedral angle, and in both cases we predict nonplanar global energy minima and large amplitude torsional motions at room temperature. In other words, the presence of a single neighboring chain induces significant deviations from planarity in oligothiophenes. However, in the environment of crystalline 6T, the trend in predicted torsional potentials match those of isolated chains, but the force constants associated with torsional motions increase by an order of magnitude. Consequently, although individual oligothiophene chains are torsionally flexible and model stacked dimers exhibit extreme deviations from planarity, in crystalline 6T these oligomers are predicted to adopt planar configurations with a steep energetic cost associated with torsional defects.