Synthesis and self-assembly of amphiphilic polyphosphazene with controllable composition via two step thiol-ene click reaction

Sequential thiol-ene click reaction is reported for amphiphilic glycosylated polyphosphazene. Poly[bis(allylamino)phosphazene] was used as precursor to go through UV irradiation with 2,3,4,6-tetra-O-acetyl-1-thiol-β-D-glucopyranose (SH-GlcAc4) and 1-dodecanethiol in sequence. Variation of the reaction conditions, including click reaction time and the dose of photoinitiator, led to different hydrophilic/hydrophobic ratios. As a result, glycosylated polyphosphazenes were synthesized with 53.3%, 77.7% and 85.0% of glucose moieties. The different residual composition could give rise to different self-assembly behaviors. Micelles of amphiphilic polyphosphazenes were formed in aqueous solution and the CMC value (0.79 × 10−3–4.00 × 10−3 mg/mL) as well as mean diameter (170–220 nm) varied along with the hydrophilic glucose moiety/hydrophobic dodecyl moiety ratio.