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Multi-olefin containing polyethers and triazolinediones : a powerful alliance

(2019) POLYMER CHEMISTRY. 10(34). p.4699-4708
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Organization
Abstract
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.
Keywords
SPEED ANIONIC-POLYMERIZATION, DIELS-ALDER REACTION, PROPYLENE-OXIDE, THERMOPLASTIC ELASTOMERS, CLICK CHEMISTRY, GLYCIDYL ETHER, POLYMERS, FUNCTIONALIZATION, ULTRAFAST, MONOMER

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Citation

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MLA
Johann, Tobias, et al. “Multi-Olefin Containing Polyethers and Triazolinediones : A Powerful Alliance.” POLYMER CHEMISTRY, vol. 10, no. 34, 2019, pp. 4699–708.
APA
Johann, T., Houck, H., Dinh, T., Kemmer-Jonas, U., Du Prez, F., & Frey, H. (2019). Multi-olefin containing polyethers and triazolinediones : a powerful alliance. POLYMER CHEMISTRY, 10(34), 4699–4708.
Chicago author-date
Johann, Tobias, Hannes Houck, Thi Dinh, Ulrike Kemmer-Jonas, Filip Du Prez, and Holger Frey. 2019. “Multi-Olefin Containing Polyethers and Triazolinediones : A Powerful Alliance.” POLYMER CHEMISTRY 10 (34): 4699–4708.
Chicago author-date (all authors)
Johann, Tobias, Hannes Houck, Thi Dinh, Ulrike Kemmer-Jonas, Filip Du Prez, and Holger Frey. 2019. “Multi-Olefin Containing Polyethers and Triazolinediones : A Powerful Alliance.” POLYMER CHEMISTRY 10 (34): 4699–4708.
Vancouver
1.
Johann T, Houck H, Dinh T, Kemmer-Jonas U, Du Prez F, Frey H. Multi-olefin containing polyethers and triazolinediones : a powerful alliance. POLYMER CHEMISTRY. 2019;10(34):4699–708.
IEEE
[1]
T. Johann, H. Houck, T. Dinh, U. Kemmer-Jonas, F. Du Prez, and H. Frey, “Multi-olefin containing polyethers and triazolinediones : a powerful alliance,” POLYMER CHEMISTRY, vol. 10, no. 34, pp. 4699–4708, 2019.
@article{8638805,
  abstract     = {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.},
  author       = {Johann, Tobias and Houck, Hannes and Dinh, Thi and Kemmer-Jonas, Ulrike and Du Prez, Filip and Frey, Holger},
  issn         = {1759-9954},
  journal      = {POLYMER CHEMISTRY},
  keywords     = {SPEED ANIONIC-POLYMERIZATION,DIELS-ALDER REACTION,PROPYLENE-OXIDE,THERMOPLASTIC ELASTOMERS,CLICK CHEMISTRY,GLYCIDYL ETHER,POLYMERS,FUNCTIONALIZATION,ULTRAFAST,MONOMER},
  language     = {eng},
  number       = {34},
  pages        = {4699--4708},
  title        = {Multi-olefin containing polyethers and triazolinediones : a powerful alliance},
  url          = {http://dx.doi.org/10.1039/c9py00718k},
  volume       = {10},
  year         = {2019},
}

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