Supramolecular polymers can exhibit highly sensitive responses to subtle changes in molecular structure and intermolecular interactions, making them useful systems for investigating the origins and control of supramolecular chirality. Building on previous work demonstrating strong induction of asymmetry in an achiral perylene diimide (a-PDI) system with the addition of small chiral molecules, this project explored how structural modifications to chiral additives influence supramolecular assembly and asymmetric amplification. A series of chiral molecules derived from (S)-citronellol were synthesized to systematically vary three structural features: carbon-chain length, saturation, and functional group. The resulting compounds were thoroughly purified and characterized using proton and carbon nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and gas chromatography–mass spectrometry (GC-MS). The chiral molecules were then combined with a-PDI in decalin and analyzed using circular dichroism (CD) spectroscopy to evaluate their effects on the supramolecular assembly and induced chirality of the supramolecular polymer. These experiments provided insight into the sensitivity of the a-PDI system to small structural changes in its chiral environment. Comparison across the molecular series provides a systematic framework for identifying the structural features of small chiral additives that are important for effective asymmetric induction. Overall, this work establishes a library of structurally related chiral molecules and provides a platform for developing structure–property relationships governing asymmetric amplification and helicity in supramolecular polymers. These findings may also guide the rational design of chiral additives and provide a foundation for future studies aimed at controlling supramolecular chirality through targeted molecular modifications.