Materials All reaction solvents used were HPLC quality and purchased form Sigma Aldrich. All NMR solvents were purchased from Cambridge Isotope Laboratories, Inc. and used without further purification. 2,2-bis(hydroxymethyl) propionic acid (Bis-HPA), Amberlyst® 15 Hydrogen Form (A-15), allyl glycidyl ether (AGE), anhydrous Iso-amyl alcohol (IAOH), 3,6-Dioxa-1,8octanedithiol, Nile red, Coumarin 30, and 2,2-dimethoxy-2-phenylacetophenone (DMPA) were purchased from Sigma Aldrich and used without further purification. A sulfo-cyanine 3 carboxylic acid dye (Cy3 dye) was purchased from Lumiprobe Corporation and used without further purification. Glycidol (GLY) was purchased from Sigma Aldrich and vacuum distilled prior to use. Thiol PEG Thiol (HS-PEG-SH) (1,500 g/mol) was purchased from Nanocs and used without further purification. 2,2'-Azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride (VA-044) was purchased from Wako chemicals and used without further purification. Tin(II) trifuoromethane sulfonate, Sn(OTf)2, was purchased from Strem Chemicals Inc. and used without further purification. Teflon sheets were obtained from ePlastics. Dialysis membranes (Spectra/Por® 7, molecular weight cut-off (MWCO): 1,000 Da) were obtained from Spectrum Laboratories, Inc. 5methyl-5-allyloxycarbonyl-1,3-dioxane-2-one (MAC), and 5-methyl-5-ethyloxycarbonyl-1,3dioxane-2-one (MEC) were synthesized according to the literature and recrystallized prior to use. 1, 2 MEC/MAC copolymers were prepared according to our work previously published with molecular weights of 4000-4300 and PDI's of 1. 3 Characterization 1 H NMR and 13 C NMR spectra were obtained from a Bruker 600 MHz Spectrometer, with CDCl3/TMS or MeOD4 as the solvent. Gel permeation chromatography (GPC) was carried out with a Waters chromatograph system equipped with a Waters 2414 refractive index detector, a Waters 2481 dual λ absorbance detector, a Waters 1525 binary HPLC pump, and four 5 mm Waters columns (300 mm x 7.7 mm), connected in series with increasing pore size (100, 1000, 100,000 and 1,000,000 Ǻ respectively). All runs were performed with dimethylformamide (DMF) with LiBr (1 mg/mL) for the polyglycidol co-polymers using polyethylene glycol standards or tetrahydrofuran (THF) for the polycarbonates using polystyrene standards as the eluent at a flow rate of 1 mL/min.