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| - Steady-State Fluorescence-Based Investigation of theInteraction between Protected Thiols and GoldNanoparticles
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| - The first demonstration of thioester and thiocarbonate binding to gold is provided via steady-statefluorescence spectroscopy of probe molecule adsorption onto a nanoparticle surface. Both thioester 1 andthiocarbonate 2 bind noncovalently to gold from aqueous solution, with 2 possessing a greater affinity forthe gold surface relative to 1. The surface-bound molecules assemble into high packing densities comprisingmolecular footprints of 24.5 ± 1.0 Å2 per molecule. Both 1 and 2 deprotect catalytically on the gold surfaceto yield hydrolysis products and surface-bound thiolate. This process is thermally activated and can bedescribed by an Arrhenius-type expression with activation energies of 14.0 and 16.7 kcal/mol for 1 and2, respectively. The results presented herein demonstrate the role of gold in catalyzing thioester andthiocarbonate hydrolysis and diversify the synthetic repertoire of organosulfur functional groups that canbe used for binding to gold.
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