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Adaptation of dynamic covalent systems of imine constituents to medium change by component redistribution under reversible phase separation.

Journal of the American Chemical Society (2012-07-13)
Nema Hafezi, Jean-Marie Lehn
ABSTRACT

A dynamic covalent library of interconverting imine constituents, dissolved in an acetonitrile/water mixture, undergoes constitutional reorganization upon phase separation induced by a physical stimulus (heat) or a chemical effector (inorganic salt, carbohydrate, organic solvent). The process has been made reversible, regenerating the initial library upon phase reunification. It represents the behavior of a dynamic covalent library upon reversible phase separation and its adaptation to a phase change, with up-regulation in each phase of the fittest constituents by component selection. Finally, the system exemplifies the splitting of a 2D (square) constitutional dynamic network into a 3D (cube) one.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Acetonitrile, suitable for HPLC, gradient grade, ≥99.9%
Sigma-Aldrich
Sodium hydroxide, ACS reagent, ≥97.0%, pellets
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Hydrochloric acid, 36.5-38.0%, BioReagent, for molecular biology
Sigma-Aldrich
Sucrose, for molecular biology, ≥99.5% (GC)
Sigma-Aldrich
Diethyl ether, ACS reagent, anhydrous, ≥99.0%, contains BHT as inhibitor
Sigma-Aldrich
Acetonitrile, suitable for HPLC, gradient grade, ≥99.9%
Sigma-Aldrich
Pyridoxal 5′-phosphate hydrate, ≥98%
Sigma-Aldrich
Lithium perchlorate, ACS reagent, ≥95.0%
Sigma-Aldrich
Tryptamine, ≥97%