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Synthesis of ferrocene-functionalized monomers for biodegradable polymer formation

  • Author(s): Upton, BM
  • Gipson, RM
  • Duhović, S
  • Lydon, BR
  • Matsumoto, NM
  • Maynard, HD
  • Diaconescu, PL
  • et al.

Cyclic carbonate and δ-valerolactone substrates functionalized with ferrocene were synthesized via alkyne-azide "click" cycloaddition. The cyclic carbonates were polymerized using 1,8-diazabicycloundec-7-ene, 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea, and benzyl alcohol. The resulting polymers were characterized by GPC, NMR spectroscopy, and cyclic voltammetry studies. It was found that polycarbonate molecular weights fall in the range of 4.1-5.2 × 103 g mol-1 with polydispersities as low as 1.26. Electrochemistry studies allowed us to identify the monomer/polymer pair with the most desirable redox potential for biological studies.

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