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Self Assembled Cages with Mechanically Interlocked Cucurbiturils.

ABSTRACT: We report preparation of (bis)aniline ligand 4 which contains a central viologen binding domain and its subcomponent self-assembly with aldehyde 5 and Fe(OTf)₂ in CH₃CN to yield tetrahedral assembly 6. Complexation of ligand 4 with CB[7] in the form of CB[7]•4•2PF₆ allows the preparation of assembly 7 which contains an average of 1.95 (range 1-3) mechanically interlocked CB[7] units. Assemblies 6 and 7 are hydrolytically unstable in water due to their imine linkages. Redesign of our system with water stable 2,2'-bipyridine end groups was realized in the form of ligands 11 and 16 which also contain a central viologen binding domain. Self-assembly of 11 with Fe(NTf₂)₂ gave tetrahedral MOP 12 as evidenced by ¹H NMR, DOSY, and mass spectrometric analysis. In contrast, isomeric ligand 16 underwent self-assembly with Fe(OTf)₂ to give cubic assembly 17. Precomplexation of ligands 11 and 16 with CB[7] gave the acetonitrile soluble CB[7]•11•2PF₆ and CB[7]•16•2PF₆ complexes. Self-assembly of CB[7]•11•2PF₆ with Fe(OTf)₂ gave tetrahedron 13 which contains on average 1.8 mechanically interlocked CB[7] units as determined by ¹H NMR, DOSY, and ESI-MS analysis. Self-assembly of CB[7]•16•2PF₆ with Fe(OTf)₂ gave cube 13 which contains 6.59 mechanically interlocked CB[7] units as determined by ¹H NMR and DOSY measurements.

SUBMITTER: Brady KG

PROVIDER: S-EPMC8340875 | biostudies-literature |

REPOSITORIES: biostudies-literature

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