Surface Modification of Bombyx mori Silk Fibroin Film via Thiol-ene Click Chemistry

Abstract

The purpose of this work is to develop a strategy for the surface modification of Bombyx mori silk fibroin (SF) film, via a thiol-ene click reaction, in order to expand its potential applicability. To achieve this goal, terminal thiol groups, from reduced glutathione, were introduced onto the surface of the SF film via a carbodiimide coupling reaction. These immobilized thiol groups act as robust crosslinkers and allow us to rapidly functionalize the surface with alkene group-containing molecules via ultraviolet (UV) light-initiated thiol-ene click chemistry. The X-ray photoelectron spectroscopy results specifically determined that alkene group-containing molecules and UV illumination are required for the thiol-ene click modification to take place on thiolated SF films. Fourier-transform infrared spectroscopy characterization of SF films indicated that the β-sheet conformation of SF was hampered throughout the modification process. Furthermore, it was found that the processes for thiol-ene click chemistry that took place on the SF film surface did not affect the thermal stability of SF films significantly, indicating the developed strategy preserved the intrinsic properties of the SF film. Taking into account that many alkene-containing molecules are suitable for thiol-ene click chemistry, we see immense potential for the incorporation of SF films into various applications, using this methodology.