bm9b00504_si_001.pdf (663.27 kB)
Azide-Substituted Polylactide: A Biodegradable Substrate for Antimicrobial Materials via Click Chemistry Attachment of Quaternary Ammonium Groups
journal contribution
posted on 2019-08-20, 14:35 authored by Pranav P. Kalelkar, Zhishuai Geng, M. G. Finn, David M. CollardPolylactide (PL)
co-polymers substituted with pendant azide groups
(azido-PL) were synthesized by the nucleophilic conjugate addition
of 3-azido-1-propanethiol to a co-polymer of PL containing α,β-unsaturated
ester units, poly(lactide-co-methylene glycolide)
(ene-PL) that is obtained from the base-promoted dehydrochlorination
of poly(lactide-co-chlorolactide) (chloro-PL). Alternatively,
azido-PL was prepared by the treatment of chloro-PL with 3-azido-1-propanethiol
without isolation of the ene-PL intermediate. The azido-PL was functionalized
by copper-catalyzed [3 + 2] cycloaddition reactions with four alkynes:
propargyl 4-methoxybenzoate, N,N,N-trimethyl-N-propargylammonium
bromide, N,N-dimethyl-N-octyl-N-propargylammonium bromide, and N,N,N-trioctyl-N-propargylammonium bromide. Polymer adducts with N,N,N-trioctyl-N-propargylammonium bromide displayed potent antimicrobial
activity both in suspension and as a polymer film.