Brønsted base mediated one-pot synthesis of catechol-ended amphiphilic polysarcosine-b-poly(N-butyl glycine) diblock copolypeptoids

Abstract

Abstract Catechol moiety offers a versatile platform in the preparation of functionalized polymers, but it is not usually compatible with catalysis in polymerizations. To address these challenges, we suggest employment of one Brønsted base in masking the activity of catechol moiety and to modulate the polymerization. Based on this strategy, the ring-opening polymerization (ROP) of sarcosine N-carboxyanhydrides (Sar-NCA) was carried out using dopamine hydrochloride as an initiator and triethylamine as a Brønsted base. PSar with predicted molecular weights (M n,NMR=3.7 kg mol−1) and narrow dispersities (Đ<1.13) was prepared. Catechol initiator was successfully linked to PSar end as confirmed by MALDI-ToF MS. Subsequently, copolymerization of N-butyl glycine N-carboxyanhydrides (Bu-Gly-NCA) from the PSar in one-pot produced catechol end-functionalized amphiphilic polysarcosine-block-poly(N-butyl glycine) diblock copolypeptoids (cat-PSar-b-PGlyBu). Further, cat-PSar-b-PGlyBu enabled the aqueous dispersion of manganese oxide nanoparticles which was attributable to the anchor of the diblock copolymers onto the surface of the nanoparticles. The strategy for catechol masking and polymerization mediating by one Brønsted base offered a new avenue into the synthesis of catechol-ended block copolymers.