ma0c01305_si_003.cif (2.26 MB)
Synthesis of Functionally and Stereochemically Diverse Polymers via Ring-Opening Metathesis Polymerization of Derivatives of the Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial Scale
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posted on 2020-06-30, 16:23 authored by Martin G. Banwell, Xin Liu, Luke A. Connal, Michael G. GardinerThe commercially available, abundant
and homochiral cellulose pyrolysis
product levoglucosenone (LGO) together with the readily derived isolevoglucosenone
(isoLGO) form, in a stereoselective manner, Diels–Alder adducts
with cyclopentadiene (CPD). These ring-fused norbornene systems, each
of which incorporates six centers of chirality and is pseudoenantiomeric
in nature, undergo ring-opening metathesis polymerization (ROMP) in
the presence of a range of ruthenium-based catalysts to produce polymers
embodying both carbo- and heterocyclic motifs. Under such conditions,
controlled polymerizations take place with target molecular weights
matching the theoretical ones and with low dispersities (from 1.1
to 1.4) normally being observed. Reduction of the carbonyl group in
the Diels–Alder adduct derived from LGO provides the corresponding
epimeric alcohols that can be etherified and the resulting ethers,
including fluorine-containing ones, also yield well-controlled polymers
via ROMP. This thus represents an efficient method for producing stereochemically
and functionally diverse polymers from a renewable feedstock available
at an industrial scale. These polymerizations are living ones as demonstrated
by the facile preparation of block copolymers from the two Diels–Alder
adducts.
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CPDcarbonyl groupRing-Opening Metathesis PolymerizationBiomass-Derived Platform Molecule L...ruthenium-based catalystsadductwell-controlled polymersheterocyclic motifsROMPDielhomochiral cellulose pyrolysis prod...ring-opening metathesis polymerizationring-fused norbornene systemsLGOStereochemically Diverse PolymersIndustrial Scaleepimeric alcoholsstereoselective mannerblock copolymersfluorine-containing ones
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