Synthesizing Functional Polymeric Materials

All reagents used in this study were purchased from Sigma-Aldrich (Saint Quentin Fallavier, France) unless otherwise noted. 2,2-bis(hydroxymethyl)propionic acid (bis-MPA, 98%), p-toluenesulfonic acid monohydrate (PTSA.H₂O, >98.5%), 4-(dimethylamino)pyridine (DMAP, 99%), Dowex^®50WX8 hydrogen form (50–100 mesh), ethyl chloroformate (97%), 8-diazabicyclo[5.4.0]undec-7-ene (DBU, 98%), benzoic acid (99.5%), acetone (99.9%), dichloromethane (DCM, 99.5%), tetrahydrofuran (THF, 99.9%), diethyl ether (99%), methanol (CH₃OH, 99.8%), water (HPLC grade), N,N-dimethyl formamide (DMF, 99.9%), diethyl (3-bromopropyl)phosphonate (95%), copper(I) bromide (CuBr, 98%), N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDETA, 99%), sodium azide (NaN₃, 99%), and dimethyl (2-hydroxyethyl)phosphonate (95%) were purchased from Acros Organics (Geel, Belgium). 2,2-dimethoxypropane (>98%), N,N’-dicyclohexyldicarbodiimide (DCC, >98%), and triethylamine (TEA, >99%) were purchased from TCI (Zwijndrecht, Belgium). Benzyl alcohol (BnOH, 99%, Alfa Aesar, Karlsruhe, Germany) and dialysis membrane (Standard RC, 3500 Da, Spectrum Laboratories, Racho Dominguez, CA, USA) were used as received. 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 5-methyl-5-propargylxycarbonyl-1,3-dioxane-2-one (MPC) were synthesized according to the literature procedures [19 (link),20 (link),21 (link)].