As oligomers and their monomeric precursors often share the same or similar O:C ratio, it would be challenging to speciate them using this parameter that is otherwise widely used to describe the overall polarity and properties of organic aerosol particles. Our findings indicate that particle surface properties resulting from the presence of αpinene derived dimer species depend in part on the backbone stereochemistry of the oligomeric compounds. Based on our results, climate models may be underestimating cloud activation in scenarios where both enantiomers of a monomeric precursor are present, such as (+)-and (-)-apinene, allowing for the formation of various dimers in different quantities that exhibit different surface activities. One can also consider higher-order oligomers, where the potential for increased variability between monomer stereochemistry and a greater dependence on atmospheric enantiomeric excess may have a more significant impact on SOA properties than is currently understood. The possibility that changes in enantiomeric excess triggered by plant stress or other exogenous influences could enhance or diminish cloud activation over a forest region may also be considered. Our future synthetic efforts will seek to address this topic by targeting higher order oligomers of differing backbone stereochemistry. In addition, determining the formation rates of specific oligomers in SOA with stereochemical specificity will be essential to better quantify the relationship between atmospheric enantiomeric excess and cloud activation. Given the ample data on how chirality can be used to control properties of polymeric materials and the critical importance of enantiopurity in drug action, particle measurements of viscosity and LLPS should also be performed to determine how they are influenced by molecular chirality. Moreover, surfacespecific measurements are needed to determine how stereochemistry influences interfacial configuration and orientation of these molecules. Access to the standards highlighted in this work will help to enable such endeavors.