Adsorption-driven self-sorting of dynamic imine libraries

Abstract

Differences in adsorption among the components of complex mixtures play a role in separations, surface-based sensing, and heterogeneous catalysis, and have been implicated in theories of the origin of life. Herein, we consider mixtures of imines and we show that if such complex mixtures are also dynamic-that is, if their components equilibrate among themselves-then they can dramatically simplify in composition during the course of column chromatography. As they travel down the column, imines continuously trade their aldehyde and amine constituents, favoring the formation of molecules with extremes of polarity at the expense of species with intermediate polarities. Iterative application of this principle leads to simplification of imine libraries containing up to 16 members into 4 major products.

Keywords: chemoselectivity; column chromatography; dynamic combinatorial chemistry; self-sorting; systems chemistry.