Polymerization of a Photocleavable Monomer Using Visible Light

Macromol Rapid Commun. 2016 Jun;37(11):905-10. doi: 10.1002/marc.201600127. Epub 2016 Apr 28.

Abstract

The polymerization of the photocleavable monomer, o-nitrobenzyl methacrylate (NBMA), is investigated using photoinduced electron/energy transfer reversible addition-fragmentation chain transfer polymerization. The polymerizations under visible red (λ max = 635 nm, 0.7 mW cm(-2) ) and yellow (λ max = 560 nm, 9.7 mW cm(-2) ) light are performed and demonstrate rational evidence of a controlled/living radical polymerization process. Well-defined poly(o-nitrobenzyl methacrylate) (PNBMA) homopolymers with good control over the molecular weight and polymer dispersity are successfully synthesized by varying the irradiation time and/or targeted degree of polymerization. Chain extension of a poly(oligo(ethylene glycol) methyl ether methacrylate) macro-chain transfer agent with NBMA is carried out to fabricate photocleavable amphiphilic block copolymers (BCP). Finally, these self-assembled BCP rapidly dissemble under UV light suggesting the photoresponsive character of NBMA is not altered during the polymerization under yellow or red light. Such photoresponsive polymers can be potentially used for the remote-controlled delivery of therapeutic compounds.

Keywords: drug delivery; photocleavable monomer; photopolymerization; visible light.

MeSH terms

  • Delayed-Action Preparations / chemical synthesis
  • Delayed-Action Preparations / chemistry
  • Light*
  • Methacrylates / chemistry*
  • Photochemical Processes*
  • Polymethacrylic Acids / chemical synthesis*
  • Polymethacrylic Acids / chemistry*

Substances

  • Delayed-Action Preparations
  • Methacrylates
  • Polymethacrylic Acids