N n n n n pentamethyldiethylenetriamine

Spray-dried sulfated CNCs (prepared by sulfuric acid mediated hydrolysis of hardwood pulp) was kindly supplied by InnoTech Alberta Inc (Edmonton, AB, Canada). The spray-dried CNC powder was stored at 4 °C and used as obtained. Triethylamine (TEA), 4-dimethyl-aminopyridine (DMAP), 2-bromoisobutyryl bromide, N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA), copper (I) bromide, [2-(methacryloyloxy)ethyl] trimethylammonium chloride (METAC) (75 wt% in H₂O), 2-aminoethyl methacrylate hydrochloride (AEM), 2,2′-bipyridyl (bpy), methanol, ethanol, tetrahydrofuran (THF), acetone, and potassium bromide (KBr) were purchased from Sigma-Aldrich (St Louis, MO, USA).

Distearoylphosphatidylethanolamine–polyethylene glycol (DSPE–PEG, PEG Mw of 550 and 2000 Da) were purchased from Avanti polar lipids (Alabama, USA). Distearoylphosphatidylethanolamine (DSPE) and hydrogenated soy phosphatidylcholine (HSPC) were purchased from Lipoid (Ludwigshafen, Germany). Triethylamine (99%), 2-(methacryloyloxy)ethyl phosphorylcholine (MPC), copper(i) bromide (CuBr, 99.999%), 2-bromoisobutyryl bromide (BIBB, 98%), N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA, 99%), bovine serum albumin (BSA), anhydrous dichloromethane (DCM), and anhydrous chloroform were purchased from Sigma-Aldrich (Israel). DiR (1,1′-dioctadecyl-3,3,3′,3′-tetramethylindotricarbocyanine iodide), DiI (1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate), fetal bovine serum (FBS), and RPMI-1640 medium were purchased from Thermo Fisher Scientific (UK). Hyaluronate-DyLight 755 (2.5 MDa) was purchased from Creative PEG Works (US).

All reagents were ACS grade or higher, unless specified. Methanol, glycerol and acetonitrile were purchased from MilliporeSigma (Billerica, MA, USA). Triethylamine (TEA); 4-dimethylaminopyridine (DMAP); N,N,N′,N″,N″-pentamethyl diethylenetriamine (PMDETA, 99%); sodium phosphate monobasic (99%); sodium phosphate dibasic (99%) copper (I) chloride; copper (II) chloride and copper(I) bromide (CuCl, CuCl₂ and CuBr 99.999% trace metal basis) were purchased from Sigma-Aldrich (Munich, Germany). α-Bromoisobutyryl bromide (BIB, 98%) was purchased from Alfa-Aesar (Ward Hill, MA, USA). 1,2-epoxy-5-hexene and 2-hydroxyethylmethacrylate (HEMA, >97%, stabilized) was purchased from Acros Organic (98%, Pittsburgh, PA, USA). Bovine serum albumin (BSA, biotechnology grade) and L-(+)-ascorbic acid (AA) were purchased from Amresco (Solon, OH, USA). 2,2′-Bipyridine (Bpy) was purchased from BeanTown Chemical (Hudson, NH, USA). Iron oxide superparamagnetic nanoparticles with a 15-nm core diameter and a 5-nm coating layer functionalized with amine groups were purchased from Ocean Nanotech (San Diego, CA, USA). All water used in this work was obtained from a Thermo Fisher 18 MΩ Barnstead Smart2Pure System (Schwerte, Germany). Commercially available regenerated cellulose membranes with a nominal molecular weight cutoff of 100 kDa were purchased from MilliporeSigma (product codes: PLCHK and PCLMK).

Copper powder (Cu(0), 99.5%, 150 mesh), copper(I) chloride (CuCl, 97%), copper(I) bromide (CuBr, 99%), N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA), alumina (Al₂O₃ neutral), benzyl alcohol (BzOH), 4-vinylbenzyl chloride (VBC), styrene (St), and tert-butyl acrylate (tBA, 98%) were purchased from Sigma–Aldrich (St. Louis, MO, USA) . 2-Bromoisobutyryl bromide (BiB, 97%), ε-caprolactone (CL, 98%), tin(II) 2-ethylhexanoate (Sn(oct)₂), and triethylamine (TEA, 99.5%) were purchased from Acros (Geel, Belgium). All solvents and monomers were purified and stored with dried molecular sieves prior to use.