Molecules with Shape Memory Based on Restricted Rotation

[reaction--see text] Diimide 1 and octaimide 2 both adopt two stable conformations at room temperature as a result of restricted rotation about two C(aryl)-N(imide) single bonds, a compact "folded" and an open "unfolded" structure. Predictable ratios of folded and unfolded rotamers can be achieved by heating in solvents of appropriate polarity as measured by the Reichardt's parameter (E(T30)). On cooling to room temperature, the resulting conformational changes are "locked in" as restricted rotation is reestablished.