Halogen bonding (XB) is an orthogonal, electrostatic interaction between a region of positive electrostatic potential (δ+) on a halogen atom (XB donor) and a Lewis base (δ-) (XB acceptor). While fundamental exploration of halogen bonding (XB) continues to be of interest, research is also beginning to harness the molecular interaction for potential applications in supramolecular chemistry, medicinal chemistry and materials science. For the latter field, the coupling of XB interactions with the unique properties of metallic nanoparticles provides a framework with which to develop XB-based molecular detection schemes. To do so, ligands able to promote XB need to be synthesized and subsequently used to functionalize nanoparticles. Herein, a synthetic scheme for a thiol molecule with XB donor capability is presented with electrochemical, NMR, IR, and HRMS characterization. The thiol, featuring a -C<sub>6</sub>F<sub>4</sub>I moiety, is used to functionalize alkanethiolate-protected gold nanoparticles through place-exchange reactions and subsequently characterized with microscopy, electrochemistry, and NMR spectroscopy. Both UV-Vis and DOSY NMR measurements are used to show XB-induced aggregation events with a targeted analyte and establish the viability of using these materials in molecular detection schemes based on strong XB interactions.

Functionalized gold nanoparticles with halogen bonding capability – an avenue for molecular detection schemes

ACS Spring 2022

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