TY - JOUR
T1 - Postfunctionalization of polyoxanorbornene backbone through the combination of bromination and nitroxide radical coupling reactions
AU - Atici, Lale Nur
AU - Demirel, Erhan
AU - Tunca, Umit
AU - Hizal, Gurkan
AU - Durmaz, Hakan
N1 - Publisher Copyright:
© 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2381-2389.
PY - 2015/10/15
Y1 - 2015/10/15
N2 - The brominated backbone of poly(oxanorbornene imide) (PONB) (PONB-Br) was functionalized with 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-acrylate, -epoxy, and poly (ethylene glycol) (PEG) yielding PONB-acrylate, PONB-epoxy, and PONB-PEG through the nitroxide radical coupling (NRC) reaction. Although an excess amount of functional-TEMPOs were used. The observed NRC efficiencies were found in the range of 7-25%. Notably, 1H NMR spectra of all polymers exhibited a signal at 6.08 ppm after NRC reactions indicating rebuilding of the main chain double bond and further identified by 13C NMR analysis. The inevitable formation of double bond through the tendency of the recombination of the formed radicals was supported by a separate experiment conducted without utilizing functional-TEMPO. Besides, the versatility of the ROMP backbone further demonstrated by the introduction hetero functionality onto the polymer by a consecutive reactions.
AB - The brominated backbone of poly(oxanorbornene imide) (PONB) (PONB-Br) was functionalized with 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-acrylate, -epoxy, and poly (ethylene glycol) (PEG) yielding PONB-acrylate, PONB-epoxy, and PONB-PEG through the nitroxide radical coupling (NRC) reaction. Although an excess amount of functional-TEMPOs were used. The observed NRC efficiencies were found in the range of 7-25%. Notably, 1H NMR spectra of all polymers exhibited a signal at 6.08 ppm after NRC reactions indicating rebuilding of the main chain double bond and further identified by 13C NMR analysis. The inevitable formation of double bond through the tendency of the recombination of the formed radicals was supported by a separate experiment conducted without utilizing functional-TEMPO. Besides, the versatility of the ROMP backbone further demonstrated by the introduction hetero functionality onto the polymer by a consecutive reactions.
KW - 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)
KW - bromination
KW - Controlled/living polymerization (CLP)
KW - IR spectroscopy
KW - nitroxide radical coupling (NRC)
KW - poly (oxanorbornene imide) (PONB)
KW - post-functionalization
KW - ring-opening metathesis polymerization (ROMP) and NMR
KW - UV spectroscopy
UR - http://www.scopus.com/inward/record.url?scp=84940722305&partnerID=8YFLogxK
U2 - 10.1002/pola.27697
DO - 10.1002/pola.27697
M3 - Article
AN - SCOPUS:84940722305
SN - 0887-624X
VL - 53
SP - 2381
EP - 2389
JO - Journal of Polymer Science, Part A: Polymer Chemistry
JF - Journal of Polymer Science, Part A: Polymer Chemistry
IS - 20
ER -