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Kinetic and Thermodynamic Modulation of Dynamic Imine Libraries Driven by the Hexameric Resorcinarene Capsule

Stefania Gambaro, Carmen Talotta, Paolo Della Sala, Annunziata Soriente, Margherita De Rosa, Carmine Gaeta, Placido Neri

2020Journal of the American Chemical Society48 citationsDOIOpen Access PDF

Abstract

The composition of dynamic covalent imine libraries (DCL) adapts to the presence of the hexameric resorcinarene capsule. In the presence of the self-assembled capsule, a kinetic and thermodynamic modulation of the imine constituents of the DCLs was observed, which was induced by an unusual predatory action of the capsule on specific imine constituents. More complex 2 × 2 DCLs also adapt to the presence of the hexameric capsule, showing a thermodynamic and kinetic modulation of the constituents induced by the predatory action of the capsule. By cross-referencing experimental data, a good selectivity (up to 66%) for one constituent can be induced in a 2 × 2 DCL.

Topics & Concepts

ChemistryImineResorcinareneCapsuleKinetic energyKinetic controlCovalent bondStereochemistrySelectivityOrganic chemistryMoleculeCatalysisPhysicsQuantum mechanicsBotanyBiologySupramolecular Chemistry and ComplexesChemical Synthesis and AnalysisCrystallography and molecular interactions
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