Monofunctional and Telechelic Polyethylenes Carrying Phosphonic Acid End Groups

Monofunctional or telechelic polyethylenes (PEs) carrying phosphonic acid end groups are obtained from functional PE produced by catalyzed chain growth (CCG) on magnesium. CCG is first used to produce iodo-end-functionalized PE (PE-I) that is efficiently turned into phosphonate end-functionalized PE (PE-P(O)(OEt)₂ ) in the presence of triethylphosphite through the Michaelis-Arbuzov reaction. A simple treatment of the resulting PE-P(O)(OEt)₂ with bromotrimethylsilane leads to the targeted phosphonic acid end-functionalized PE (PE-P(O)(OH)₂ ) for the first time. Vinyl-end-functionalized analogs (Vin-PE-P(O)(OEt)₂ ) are produced using vinyl-end-functionalized PE-I (Vin-PE-I) recently obtained through CCG. A cross-metathesis reaction is then employed to couple Vin-PE-P(O)(OEt)₂ and produce after treatment with bromotrimethylsilane the corresponding unprecedented α-ω-(diphosphonic acid) telechelic PE ((OH)₂ (O)P-PE-P(O)(OH)₂ ).