10.1021/la4005856.s001 Lijia Liu Lijia Liu Timothy L. Kelly Timothy L. Kelly Phase Transfer of Triangular Silver Nanoprisms from Aqueous to Organic Solvent by an Amide Coupling Reaction American Chemical Society 2013 Triangular Silver Nanoprisms diphenylamine phase transfer dicyclohexylamine AgNPr amines carboxylic acid end chloroform aggregation MHA amide 2013-06-11 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Phase_Transfer_of_Triangular_Silver_Nanoprisms_from_Aqueous_to_Organic_Solvent_by_an_Amide_Coupling_Reaction/2406910 In this paper, we describe a procedure for the phase transfer of silver nanoprisms (AgNPrs) from aqueous solution to chloroform via an amide coupling reaction. AgNPrs are first modified with 16-mercaptohexadecanoic acid (MHA), and then primary or secondary amines are attached to the carboxylic acid end of the MHA ligand through a carbodiimide-mediated amide coupling step. Secondary amines, such as dicyclohexylamine and diphenylamine, are found to solubilize the nanoparticles in chloroform, whereas primary amines (e.g., butylamine and hexadecylamine) do not result in phase transfer. It is found that the AgNPrs functionalized with dicyclohexylamine show the highest stability and the least aggregation after undergoing phase transfer; in contrast, with a less nucleophilic amine, such as diphenylamine, the amide coupling reaction does not go to completion and the resultant AgNPrs are less stable and more prone to aggregation.