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Postfunctionalization of polyoxanorbornene backbone through the combination of bromination and nitroxide radical coupling reactions

Author:
Atici, Lale Nur, Demirel, Erhan, Tunca, Umit, Hizal, Gurkan, Durmaz, Hakan
Source:
Journal of polymer science 2015 v.53 no.20 pp. 2381-2389
ISSN:
0887-624X
Subject:
bromination, free radicals, nuclear magnetic resonance spectroscopy, polyethylene glycol
Abstract:
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. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2381–2389
Agid:
4084862