Supramolecular Immobilization of Adamantyl and Carboxylate Modified N-Heterocyclic Carbene Ligand on Cucurbituril Substrates

Herein, the design, synthesis, supramolecular interactions and structural analysis of a novel bidentate carboxylate chelating N-heterocylic carbene (NHC) ligand is presented. The NHC structure was modified to strategically incorporate adamantyl moiety for the formation of a supramolecular complex with host molecules such as cucurbiturils. The adamantyl modified NHC ligand could potentially be used in recoverable homogeneous catalysts when Immobilized on a solid support via host-guest chemistry. As a versatile precursor, NHC ligand (8) was synthesized and characterized by ¹H-NMR, ¹³C-NMR, FTIR, single crystal x-ray crystallography and elemental analysis. A proof-of-principle non-covalent immobilization of the NHC ligand (8) with a Cucurbit[7]uril (CB7) host was demonstrated using ¹H-NMR titration.