To prepare thiol protected aqueous gold nanoparticles (~ 5 nm) we normally perform ligand exchange with citrate capped AuNPs. These thiol like p-MBA (para-mercaptoubenzoic acid) or LA (lipoid acid) are normally insoluble in H20, need to add base to prepare stock solution; but these thiol capped AuNPs show totally opposite solubility ––soluble in H20, insoluble in organic solvent. What makes these clusters insoluble in organic solvent?

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