Fully degradable antibacterial poly(ester‐phosphoester)s by ring‐opening polymerization, “click” chemistry,and quaternization

Fully degradable cationic poly(ester‐phosphoester)s with antibacterial properties were prepared by a combination of ring‐opening polymerization (ROP) and “click” reaction. First, poly(ester‐phosphoester)s‐bearing alkynyl groups were synthesized by the ring‐opening copolymerization of 2‐(2‐propynyloxy)?2‐oxo‐1,3,2‐dioxaphospholane (propynyl ethylene phosphate, PEP) and ε‐caprolactone (CL) using lanthanum tris(2,6‐di‐tert‐butyl‐4‐methylphenolate)s (La(DBMP)₃) as the catalyst. 2‐Azido‐N,N‐dimethylethanamine (DMEAN₃) was then attached to the copolymers by “click” reaction, resulting in poly(ester‐phosphoester)s with pendant tertiary amines. After the quaternization reactions between the copolymer and various alkyl bromides, cationic poly(ester‐phosphoester)s containing ammonium groups were obtained. Optical density (OD) measurement shows that the cationic copolymers have excellent antibacterial activity, which makes them potential candidates as biomaterials. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42647.