期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 61, 期 33, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207418
关键词
Cavitands; Dynamic Covalent Chemistry; Dynamic Self Assembly; Porous Organic Cages; Out of Equilibrium Systems
资金
- NSF [CHE-2002781]
Living systems use chemical fuels to assemble functional structures. In this study, the dissipative formation of covalent basket cage CBC 5 by reversible reactions is described.
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(3), M-w=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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