Remarkably, in the decades of technological development in the membrane science field, design of new membrane materials has been, and remains, a largely trial-and-error process, guided by experience and intuition . Current approaches generally involve tuning chemical groups to increase affinity and solubility towards a desired gas, or incorporating greater free volume to increase overall diffusivity . When assembling a new polymer, typically a desired enhancement is targeted (i.e., higher CO2 affinity, higher overall permeability, aging resistance etc.) and a chemical group that is likely to achieve that enhancement is incorporated into the polymer chemistry . For achieving higher permeability, polymers of intrinsic microporosity (PIMs) have been extensively studied during the last two decades . PIMs generally enhance fractional free volume via inefficient chain packing to increase permeability, while simultaneously stiffening the polymer backbone and improving solubility selectivity . Efforts to design improved chemistries for PIMs generally involve tuning the contortion group, increasing steric frustration via modifications to side chains, or further stiffening the polymer backbone . Still, many of these studies remain limited to an Edisonian approach, unable to identify or utilize big-picture rules of chemistry-property relationships in polymer membranes.