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Dissipative Formation of Covalent Basket Cages. | LitMetric

Dissipative Formation of Covalent Basket Cages.

Angew Chem Int Ed Engl

Department of Chemistry & Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA.

Published: August 2022

AI Article Synopsis

Article Abstract

Living systems use chemical fuels to transiently assemble functional structures. As a step toward constructing abiotic mimics of such structures, we herein describe dissipative formation of covalent basket cage CBC 5 by reversible imine condensation of cup-shaped aldehyde 2 (i.e., basket) with trivalent aromatic amine 4. This nanosized [4+4] cage (V=5 nm , M =6150 Da) has shape of a truncated tetrahedron with four baskets at its vertices and four aromatic amines forming the faces. Importantly, tris-aldehyde basket 2 and aliphatic tris-amine 7 undergo condensation to give small [1+1] cage 6. The imine metathesis of 6 and aromatic tris-amine 4 into CBC 5 was optimized to bias the equilibrium favouring 6. Addition of tribromoacetic acid (TBA) as a chemical fuel perturbs this equilibrium to result in the transient formation of CBC 5, with subsequent consumption of TBA via decarboxylation driving the system back to the starting state.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9544755PMC
http://dx.doi.org/10.1002/anie.202207418DOI Listing

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