Technai 20

All reagents were purchased from Sigma-Aldrich and used as received unless stated otherwise. CH₂Cl₂ was distilled over calcium hydride. Styrene was washed with 1 N NaOH, followed by water to remove inhibitors, dried over MgSO₄ and then purified by vacuum distillation over calcium hydride. AIBN was recrystallized from MeOH twice prior to use. Lactose-oxime 8 was synthesized according to previously reported procedures.^{[25 (link)]} The NMR spectra were recorded on a Varian Mercury 300 MHz or Varian Inova 500 MHz spectrometers using CDCl₃ as a solvent unless stated otherwise. ¹H NMR-based M_n of dodecyl trithiocarbonate-terminated polymers was calculated by comparing the integral areas under CH_ar peaks of repeating units with integrals of CH₂–S signal of ω-chain end. The weight of CTA (566 g mol⁻¹) was then added to the sum of weights of repeating units. GPC analyses were performed on Shimadzu LC-20AD liquid chromatography instrument, equipped with RI detector. Two Waters Styragel columns (HR3 and HR4) were placed in series. THF was used as eluent at 1 mL min⁻¹ flow rate; the column oven was set to 40 °C. Molecular weights were calculated against polystyrene standards. TEM images were obtained on Philips/FEI Technai 20 instrument using copper TEM grids. A 2% (wt/vol) uranyl acetate solution was used to stain the polymeric nanoparticles before recording.