Amphiphilic photosensitive dextran-g-poly(o-nitrobenzyl acrylate) glycopolymers

Carbohydr Polym. 2016 Jan 20:136:598-608. doi: 10.1016/j.carbpol.2015.09.061. Epub 2015 Sep 25.

Abstract

Among all photosensitive monomers reported in the literature, o-nitrobenzyl acrylate (NBA) was selected in this present study. Two strategies were compared to produce azido-terminated poly(o-nitrobenzyl acrylate) (PNBA) using controlled Single Electron Transfer-Living Radical Polymerization (SET-LRP). In a parallel way, dextran (Dex) was modified by the introduction of several alkynyl-terminated hydrophobic chains. Finally, an Huisgen-type Copper (I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) click-chemistry was carried out to produce amphiphilic Dex-g-PNBA glycopolymers with different number and length of PNBA grafts. 2D DOSY (1)H NMR was used to prove the formation of such glycopolymers. Preliminary study on Dex-g-PNBA self-assembly was done by measuring the critical water content (CWC) above which Dex-g-PNBA started to auto-organize themselves to produce nano-objects. Finally, under UV irradiation, PNBA grafts turn into poly(acrylic acid) ones giving light-sensitive properties to such amphiphilic Dex-g-PNBA. Such properties were evaluated and compared with those of PNBA.

Keywords: 2-Nitrobenzyl acrylate; Biodegradable; CRP; Grafted copolymer; Photo-responsive polymer; RDRP.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • Click Chemistry
  • Dextrans / chemistry*
  • Nitrobenzenes / chemistry
  • Photosensitizing Agents / chemical synthesis*
  • Photosensitizing Agents / chemistry
  • Surface-Active Agents / chemical synthesis*
  • Surface-Active Agents / chemistry

Substances

  • Acrylates
  • Dextrans
  • Nitrobenzenes
  • Photosensitizing Agents
  • Surface-Active Agents