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Multi-olefin containing polyethers and triazolinediones: a powerful alliance

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Multi-functional polyethers with ene or diene moieties were prepared via the polymerisation of tailored functional glycidyl ether monomers to create a platform for click chemistry with triazolinediones (TADs). Specifically, two novel monomers (i) 2,4-hexadien-1-yl glycidyl ether (HDEGE) and (ii) citronellyl glycidyl ether (CitroGE), designed to undergo a Diels–Alder or Alder–Ene reaction with TADs, respectively, were synthesized and subsequently transformed into a variety of tailored polyethers, either via the monomer activated method or anionic ring opening polymerisation. Multi-functional copolymers of HDEGE with ethylene oxide, propylene oxide and ethoxy ethyl glycidyl ether as well as ABA and AB poly(ethylene glycol)-based block copolymers with CitroGE are reported to demonstrate the scope of this platform. The ene and diene moieties were reacted with both mono- and bis-funtional TAD compounds to yield quantitative and irreversible modification with adjustable reaction kinetics, ranging from seconds for the HDEGE-based polymers to several minutes for the CitroGE-based polymers. In case of bis-functional TAD compounds, network formation and rapid gelation were achieved. The herein described multi-functional polyethers based on HDEGE and CitroGE are introduced as a platform to enable facile, fast, metal-free and quantitative functionalization of polyethers under mild conditions with an adjustable reaction time span.

Graphical abstract: Multi-olefin containing polyethers and triazolinediones: a powerful alliance

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The article was received on 18 May 2019, accepted on 23 Jul 2019 and first published on 23 Jul 2019

Article type: Paper
DOI: 10.1039/C9PY00718K
Polym. Chem., 2019, Advance Article

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    Multi-olefin containing polyethers and triazolinediones: a powerful alliance

    T. Johann, H. A. Houck, T. Dinh, U. Kemmer-Jonas, F. E. Du Prez and H. Frey, Polym. Chem., 2019, Advance Article , DOI: 10.1039/C9PY00718K

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