Free radical homopolymerization of a vinylferrocene/cyclodextrin complex in water

Beilstein J Org Chem. 2010 Jun 1:6:60. doi: 10.3762/bjoc.6.60.

Abstract

We report the radical initiated homopolymerization of a soluble vinylferrocene cyclodextrin-complex in water. Uncomplexed vinylferrocene 1 and the corresponding homopolymer are hydrophobic and completely insoluble in water. Complexation of 1 with methyl-β-cyclodextrin 2 results in clearly water-soluble structures due to incorporation of the ferrocene moiety into the cyclodextrin cavity. After free radical polymerization of the water-soluble complexed monomer, corresponding to polyvinylferrocene (PVFc), the water-soluble polymer is obtained due to the host guest interactions. Those polymeric complexes are stable in water up to about 90 °C. Above this temperature the polymer precipitates due to decomplexation. The complex was investigated by ¹H NMR spectrometry, dynamic light scattering (DLS), differential scanning calorimetry (DSC), and lower critical solution temperature (LCST) measurements.

Keywords: cyclodextrin; free radical polymerization; polyvinylferrocene; vinylferrocene.