Alternating Sequence Control for Poly(ester amide)s by Organocatalyzed Ring-Opening Polymerization

Abstract

Sequence-controlled polymerization is the forefront of polymer chemistry. Herein, the feasibility of sequence regulation by using organocatalyzed ring-opening polymerization (ROP) is demonstrated. In particular, ring expansion strategy is employed to synthesize pre-organized monomers 1 and 2. ROP is conducted by using 1,5,7-triazabicyclo[4.4.0]dec-5-ene and benzyl alcohol as the catalyst and initiator, respectively. Poly(ester amide)s (PEAs) P1-P3 comprising glycolic acid, lactic acid, and 7-aminoheptanoic acid units are obtained in high molecular weights and good yields. NMR and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry results verify the microstructural integrity of P1 and P2. Differential scanning calorimetry results show that PEA without methyl branches is crystalline. Moreover, thermal stability, surface wettability, and degradation profiles of P1-P3 are also investigated.

Keywords: organocatalysis; poly(ester amide); ring expansion; ring-opening polymerization; sequence control.