Studies on the sulfation of cellulose α-lipoate and ability of the sulfated product to stabilize colloidal suspensions of gold nanoparticles

Abstract

A versatile method for the synthesis of cellulose α-lipoate with a low degree of substitution (DS) has been developed using N,N-dimethylacetamide (DMA)/LiCl as a solvent and N,N'-carbonyldiimidazole (CDI) as an esterification reagent. The cellulose α-lipoate with DS of α-lipoate groups of 0.26 was converted with sulfur trioxide-pyridine complex in dimethyl sulfoxide (DMSO) as solvent. The sulfation is accompanied by an unexpected partial oxidation of the disulfide moiety leading to the formation of the corresponding stereoisomers of S-oxides. The resulting mixture of water-soluble cellulose α- and β-lipoate sulfate possesses a DS of sulfuric acid half ester groups of 1.78. This cellulose-α/β-lipoate sulfate derivative can be used as an effective stabilizer and solubilizer for the formation of colloidal suspensions of gold nanoparticles formed in situ in aqueous solution.

Keywords: Esterification of cellulose; Gold nanoparticles; Oxidation; Sulfur-containing cellulose derivatives; Water-solubility.