Honeycomb membranes prepared from 3-O-amino acid functionalized cellulose derivatives

The development of value-added wood-derived polymer products is of significant importance. Of particular interest is the synthesis of advanced bioactive cellulosic materials. In the present research, novel cellulosic honeycomb films are reported. Cellulose was reacted with dimethylthexylsilyl chloride to form regioselective 2,6-di-O-thexyldimethylsilyl cellulose followed by substitution of the C3 with functionalized poly(ethylene glycol) (PEG). The free end of the PEG side chains of the regioselective 3-O-poly(ethylene glycol)–2,6-di-O-thexyldimethylsilyl cellulose served as an attachment point for bioactive molecules. As an example, Fmoc–Gly–OH was linked to the free end of PEG to produce 3-O-Fmoc–Gly–poly(ethylene glycol)–2,6-di-O-thexyldimethylsilyl cellulose. Honeycomb films were produced through film casting under a humid airflow. AFM analysis revealed the directed self-assembly of the 3-O-Fmoc–Gly–poly(ethylene glycol)–2,6-di-O-thexyldimethylsilyl cellulose wherein the pendent 3-O-Fmoc–Gly–poly(ethylene glycol) groups allocated preferentially around the edges of the honeycomb pores.

► We report the synthesis of regioselective amphiphilic cellulose derivatives.
► As a model amino acid compound, Fmoc–Gly–OH, was linked to the amphiphilic polymer.
► Honeycomb film was formed with the amino acid functionalized cellulose derivatives.
► Fmoc–Gly–poly(ethylene glycol) was allocated inside the honeycomb pores.
► The pore size of the films is affected by the length of the hydrophilic group.