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Rapid, regioselective living ring-opening metathesis polymerization of bio-derivable asymmetric tricyclic oxanorbornenes
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Naguib, Mohamed, Schiller, Tara L. and Keddie, Daniel J. (2018) Rapid, regioselective living ring-opening metathesis polymerization of bio-derivable asymmetric tricyclic oxanorbornenes. Macromolecular Rapid Communications, 39 (7). doi:10.1002/marc.201700794 ISSN 1022-1336.
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Official URL: http://dx.doi.org/10.1002/marc.201700794
Abstract
The synthesis of a range of alkyl esters (methyl, n‐butyl, and n‐decyl) prepared via Steglich esterification of the thermodynamically controlled exo, exo Diels–Alder adduct of furfuryl alcohol and maleic anhydride is reported. Subsequent ring‐opening metathesis polymerization of these bio‐derivable tricyclic oxanorbornene analogs delivers polymers with targeted molar mass and low molar mass dispersity. The polymerizations are rapid with complete monomer conversion achieved within 15 min. Significantly, the presence of the cyclic lactone at the bridgehead of these monomers leads to polymers with high regioregularity (>85% head‐to‐tail) and high stereoregularity (>75% trans). The resultant polymers display both high thermal stability and high glass transition temperatures. This new class of oxanorbornene monomer, accessed from bio‐derivable furfuryl alcohol and maleic anhydride, may be further tailored to incorporate a range of functional moieties. Furthermore, the exceptional properties of the derived polymers indicate potential in a range of applications.
Item Type: | Journal Article | ||||||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Engineering > WMG (Formerly the Warwick Manufacturing Group) | ||||||||||||
Library of Congress Subject Headings (LCSH): | Ring-opening polymerization, Monomers -- Synthesis, Esters | ||||||||||||
Journal or Publication Title: | Macromolecular Rapid Communications | ||||||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||||||||||
ISSN: | 1022-1336 | ||||||||||||
Official Date: | April 2018 | ||||||||||||
Dates: |
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Volume: | 39 | ||||||||||||
Number: | 7 | ||||||||||||
DOI: | 10.1002/marc.201700794 | ||||||||||||
Status: | Peer Reviewed | ||||||||||||
Publication Status: | Published | ||||||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||||||
Date of first compliant deposit: | 9 April 2018 | ||||||||||||
Date of first compliant Open Access: | 15 January 2019 | ||||||||||||
RIOXX Funder/Project Grant: |
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