Synthesis of nonsymmetric chain end functionalized polyisobutylenes |
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Authors: | Olubummo Adekunle Florian Herbst Katharina Hackethal Wolfgang H. Binder |
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Affiliation: | Institute of Chemistry, Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin‐Luther University Halle‐Wittenberg, Halle 06120, Germany |
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Abstract: | We present the synthesis of nonsymmetric α‐ω‐functionalized polyisobutylenes (PIBs) bearing different functional moieties on their chain ends. Thus, on one chain end either, a short tri‐ethylene oxide chain (TEO) or a phosphine oxide ligand is attached, whereas the other chain end is substituted by hydrogen bonding moieties (thymine/2,6‐diaminotriazine). The nonsymmetric PIBs were synthesized via living cationic polymerization using methyl‐styrene epoxide as initiator, followed by quenching reaction with 3‐bromopropyl‐benzene. Subsequent bromide/azide exchange and the use of the azide/alkyne click reaction allowed the synthesis of (a) (α)‐TEO‐(ω)‐thymine‐telechelic PIB ( 7a ), (b) (α)‐triethyleneoxide‐(ω)‐triazine telechelic PIB ( 7b ), and (c) (α)‐phosphinoxide‐(ω)‐thymine‐telechelic PIB ( 13 ) with molecular weights Mn ~ 4000 g mol?1 and low polydispersities (Mw/Mn = 1.3). The chemical identity of the final structures was proven by extensive 1H NMR investigations and matrix‐assisted laser desorption/ionization‐mass spectroscopy (MALDI). The presented method for the first time offers a simple and highly versatile approach toward supramolecular nonsymmetric α‐ω‐functionalized PIB. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 |
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Keywords: | “ click” ‐chemistry functionalization living cationic polymerization MALDI mass spectrometry nonsymmetric substitution telechelic polymer |
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