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- Title
Dissipative Formation of Covalent Basket Cages.
- Authors
Liyana Gunawardana, Vageesha W.; Finnegan, Tyler J.; Ward, Carson E.; Moore, Curtis E.; Badjić, Jovica D.
- 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 nm3, Mw=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.
- Subjects
CHEMICAL systems; BASKETS; AROMATIC amines; DECARBOXYLATION; CONDENSATION
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 33, p1
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202207418