Ring-opening reactions of backbone epoxidized polyoxanorbornene

Günay U. S., DEMIREL E., Hızal G., TUNCA Ü., DURMAZ H.

REACTIVE & FUNCTIONAL POLYMERS, vol.94, pp.35-42, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 94
  • Publication Date: 2015
  • Doi Number: 10.1016/j.reactfunctpolym.2015.07.004
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.35-42
  • Keywords: Poly(oxanorbornene imide) (PONB), Ring-opening metathesis polymerization (ROMP), Backbone epoxidation, Amine-epoxy ring-opening reaction, Thiol-epoxy ring-opening reaction, ORTHOGONAL CLICK CHEMISTRIES, METATHESIS POLYMERIZATION, POST-FUNCTIONALIZATION, BLOCK-COPOLYMERS, DIELS-ALDER, POLYMERS, ROMP, MACROMONOMERS, COMBINATION, EFFICIENT
  • Istanbul Technical University Affiliated: Yes


In this article, we report the synthesis of poly(oxanorbornene imide) (PONB) with internal epoxy groups (epoxidized-PONB30) and its ring-opening reactions with various nucleophiles, such as amine, azide, and thiols. The ring-opening reactions with amines yielded the amine-hydroxyl PONBs in the range of 36-95% of functionalization depending upon the amine content per epoxy. An allylamine-hydroxyl functionalized PONB was further functionalized efficiently with 1-octanethiol by radical thiol-ene reaction. The ring-opening reaction of the main chain epoxy using thiols resulted in a lower functionalization than amines with a similar functional group (e.g., allyl). In addition, sodium azide together with NH4Cl, was employed efficiently in the ring-opening reaction of the main chain epoxy, resulting in an azide/hydroxyl-functional PONB30 with 53% efficiency, which was determined after a model copper-catalyzed azide-alkyne cycloaddition (CuAAC) experiment was carried out. (C) 2015 Elsevier B.V. All rights reserved.