Angew Chem Int Ed Engl. 2015 Feb 09;54(7):2219-22. doi: 10.1002/anie.201409741. Epub 2014 Dec 21.

Adsorption-driven self-sorting of dynamic imine libraries.

Angewandte Chemie (International ed. in English)

Chia-Wei Hsu, Ognjen Š Miljanić

PMID: 25529461 DOI: 10.1002/anie.201409741

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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

Publication Types

• Journal Article