One-pot one-step synthesis of a photo-cleavable cross-linker via Passerini reaction for fabrication of responsive polymeric particles

Deveci G., Kahveci M. U.

POLYMER BULLETIN, vol.76, no.3, pp.1471-1487, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 76 Issue: 3
  • Publication Date: 2019
  • Doi Number: 10.1007/s00289-018-2449-0
  • Journal Name: POLYMER BULLETIN
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1471-1487
  • Bezmialem Vakıf University Affiliated: Yes

Abstract

A new approach for the synthesis of a photo-cleavable cross-linker and preparation of light-responsive polymeric particles is proposed in the current work. A multicomponent reaction, Passerini reaction, is employed as a one-pot one-step synthetic approach for the preparation of the acrylate-based cross-linker (hexane-1,6-diylbis(azanediyl))bis(1-(2-nitrophenyl)-2-oxoethane-2,1-diyl) diacrylate) (PCDA). Briefly, Passerini reaction of 1,6-diisocyanohexane, 2-nitrobenzaldehyde and acrylic acid yields the photo-cleavable diacrylate with o-nitrobenzyl ester moieties. Subsequently, the cross-linker is successfully utilized in the preparation of poly(methyl methacrylate) microspheres and nanospheres via suspension and miniemulsion polymerization, respectively. Finally, light-induced degradations of the polymeric particles are conducted under UV light illumination (around 366nm). All compounds and products in each step are well characterized by FTIR, H-1-NMR, UV-Vis spectroscopy, light microscopy and SEM.