Synthesis of 5-substituted derivatives of isophthalic acid as non-polymeric amphiphilic coating for metal oxide nanoparticles

In the course of development of novel capping ligands with variable steric factor, which will be used as an organic coating for metal oxide nanoparticles, a base-catalyzed nucleophilic oxirane ring-opening addition reaction between dimethyl 5-hydroxyisophthalate and allyl glycidyl ether was studied. The allyl-terminated 1-1, 1-2, and 1-3 adducts and dihydroxylated derivative of the 1-1 adduct, 5-diglyceroxy isophthalic acid, were synthesized. The latter binds to the surface of 5 nm γ-Fe₂O₃ nanoparticles in reaction with their surfactant-free diethylene glycol colloids.