TY - JOUR
T1 - Ring-opening reactions of backbone epoxidized polyoxanorbornene
AU - Gunay, Ufuk Saim
AU - Demirel, Erhan
AU - Hizal, Gurkan
AU - Tunca, Umit
AU - Durmaz, Hakan
N1 - Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.
PY - 2015/7/27
Y1 - 2015/7/27
N2 - 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.
AB - 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.
KW - Amine-epoxy ring-opening reaction
KW - Backbone epoxidation
KW - Poly(oxanorbornene imide) (PONB)
KW - Ring-opening metathesis polymerization (ROMP)
KW - Thiol-epoxy ring-opening reaction
UR - http://www.scopus.com/inward/record.url?scp=84937964463&partnerID=8YFLogxK
U2 - 10.1016/j.reactfunctpolym.2015.07.004
DO - 10.1016/j.reactfunctpolym.2015.07.004
M3 - Article
AN - SCOPUS:84937964463
SN - 1381-5148
VL - 94
SP - 35
EP - 42
JO - Reactive and Functional Polymers
JF - Reactive and Functional Polymers
ER -