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Supramolecular electronics provide opportunities to integrate molecular building blocks into electronic circuits, and investigations of the mechanical properties of the non‐covalent interactions are necessary to understand the role of the assembly configuration in the electronic coupling among different assembly blocks. However, the mechanical characterization of supramolecular interactions remains experimentally challenging. We investigated the strain distribution of the supramolecular interactions through a series of single‐stacking junctions. The alpha values exhibit a clear odd‐even effect versus the numbers of thiophene rings. The theoretical calculations demonstrated that a larger rotational barrier of the single‐stacking junctions with an even number of thiophene rings leads to limited torsional freedom and thus a smaller strain distribution. These results provide new insights into the control of supramolecular interactions by the design of the basic molecular building blocks. [ABSTRACT FROM AUTHOR]