The computational analysis discussed herein, details the complexities of dynamic covalent sensors that exist as a mixture of multiple equilibrating diastereomeric and conformational isomers (i.e. 16, Scheme 16A). While we have analyzed this in detail in the preceding paragraphs, the overarching conclusion can be summarized as follows. Substitution at the A-ring ortho and para positions has opposite, competing effects on the CD-signal intensity. Ortho steric bulk energetically favors one of the helical diastereomers by reinforcing a key T-stacking interaction (i.e., Figure , inset). This leads to a large, net CD-signal from exciton coupling of the energetically preferred helical chromophore. Para steric bulk, in contrast, stabilizes the minor isomer leading to a smaller energetic preference for one terpyridine helix. This means that the exciton coupling of the terpyridine chromophores with opposite helicity will largely offset one another and only a weak net CD signal will be observed. The competing roles of para and ortho substituents are also reflected in the final MLR model (Figure ). Steric bulk at the para position is reflected by the term Bmax 8.5Å and is negatively correlated to CD signal intensity, while steric bulk at the ortho position, reflected by Bmax 2Å, is positively correlated. Taken together this illuminates the following design principle. Installation of an ortho-functionalized A-ring and omission of para-substituents will maximize efficient stereochemical transfer from the hemiaminal ether stereocenter to the terpyridine helix and will thereby maximize the CD signal for chiral alcohols of this type.