Chemo-enzymatic synthesis of a levoglucosenone-derived bi-functional monomer and its ring-opening metathesis polymerization in the green solvent Cyrene

The quite recent, yet quickly expanding, norbornene-levoglucosenone-based monomer family was extended to include a novel bi-functional methacrylate monomer that can be readily synthesized through a chemo-enzymatic pathway. The norbornene moiety was selectively polymerized via ring-opening metathesis...

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Bibliographic Details
Published in:Polymer chemistry 2020-12, Vol.11 (47), p.7471-7475
Main Authors: Fadlallah, Sami, Peru, Aurélien A. M, Longé, Lionel, Allais, Florent
Format: Article
Language:English
Subjects:
Chemical Sciences
Dichloromethane
Metathesis
Monomers
Polymer chemistry
Polymerization
Polymers
Ring opening polymerization
Solvents
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Summary:The quite recent, yet quickly expanding, norbornene-levoglucosenone-based monomer family was extended to include a novel bi-functional methacrylate monomer that can be readily synthesized through a chemo-enzymatic pathway. The norbornene moiety was selectively polymerized via ring-opening metathesis polymerization (ROMP) under ambient conditions where Cyrene™ was explored for the first time as a green bio-alternative organic solvent for ROMP reactions. The activity of the metathesis catalysts was finely tuned in Cyrene™, versus common and toxic solvents such as dichloromethane, resulting in highly thermostable functional polymers with a T d5% up to 401 °C and a T g of −16.8 °C. The levoglucosenone-based norbornenes family was extended to include a new bi-functional methacrylate monomer that, upon ROMP in Cyrene™, leads to polymers with pendent methacrylate moieties which can be modified by post-polymerization reactions.
ISSN:1759-9954
1759-9962
DOI:10.1039/d0py01471k