One-pot synthesis of dendritic polyamide

Abstract

Dendritic polyamides with polydispersity of 1.1–1.4 have been successfully prepared from trimesic acid, 5-aminoisophthalic acid, and 4-aminophenylpropionic acid as a core molecule, a dendron, and a spacer unit, respectively, with a one-pot procedure. This procedure involves successive activation of end carboxyl groups with the condensing agent diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate (DBOP), followed by condensation of active amide with 5-aminoisopthalic acid or 4-aminophenylpropionic acid and, finally, capping of the end carboxyl groups with p-anisidine. The structure of dendritic polyamides was investigated by 1H-NMR spectroscopy, and it was found that the polymers obtained contained approximately 10% defects. Furthermore, the model reaction was studied to demonstrate the feasibility of dendritic polyamides. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3638–3645, 1999