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Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology. KTH, Centres, Science for Life Laboratory, SciLifeLab.ORCID iD: 0000-0002-1050-3723
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
KTH, Centres, Science for Life Laboratory, SciLifeLab. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-8727-2102
KTH, School of Engineering Sciences (SCI), Centres, VinnExcellence Center BiMaC Innovation. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.ORCID iD: 0000-0002-8348-2273
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2020 (English)In: Journal of Applied Polymer Science, ISSN 0021-8995, E-ISSN 1097-4628, Vol. 137, no 18, article id 48949Article in journal (Refereed) Published
Abstract [en]

Enzyme-catalyzed transformations have a great potential in both the pharmaceutical and chemical industry to achieve complex and (stereo)selective synthesis under mild reaction conditions. Still, the implementation of biocatalysis in the prerequisite upgrading of inert synthons into activated monomers for polymer applications has not yet been fully realized. In this contribution, we show that scaled-up synthesis of bicyclic norcamphor lactone using an engineered Baeyer–Villiger monooxygenase (BVMO) is feasible to reach complete conversion of the corresponding ketone in 24 h in shake-flask. The lactone monomer obtained by enzyme catalysis was copolymerized with ε-caprolactone via ring-opening polymerization to study the impact of the additional ring on material properties. Moreover, four-arm star-like, homo and block copolymers were designed from ε-caprolactone, ε-decalactone, and norcamphor lactone and characterized for their structural and thermal properties. These newly explored macromolecules were functionalized with furan rings using the enzyme Candida antarctica lipase B which allowed the formation of thermolabile networks via the pericyclic reaction with bismaleimide by means of Diels–Alder chemistry. The bonding/debonding state of these star-like based materials can be tuned by a suitable selection of thermal treatment. The temperature-dependent reversibility was assessed by thermal analysis and solubility test. Our results presented here shed light on the high potential of the use of chemoenzymatic approaches in the synthesis of new functional materials with tuned physiochemical properties.

Place, publisher, year, edition, pages
John Wiley and Sons Inc. , 2020. Vol. 137, no 18, article id 48949
Keywords [en]
biosynthesis of polymers, ring-opening polymerization, stimuli-sensitive polymers, Biochemistry, Block copolymers, Catalysis, Chemical bonds, Chemical industry, Enzymes, Esters, Functional materials, Ketones, Monomers, Stars, Thermoanalysis, Candida antarctica lipase B, Chemoenzymatic approaches, Mild reaction conditions, Physio-chemical properties, Polymer applications, Selective synthesis, Temperature dependent, Ring opening polymerization
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-272248DOI: 10.1002/app.48949ISI: 000506927800001Scopus ID: 2-s2.0-85077887033OAI: oai:DiVA.org:kth-272248DiVA, id: diva2:1425619
Note

QC 20200421

Available from: 2020-04-21 Created: 2020-04-21 Last updated: 2020-04-21Bibliographically approved

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Farhat, WissamBiundo, AntoninoStamm, ArneMalmström, EvaSyrén, Per-Olof

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Coating TechnologyScience for Life Laboratory, SciLifeLabVinnExcellence Center BiMaC InnovationFibre- and Polymer Technology
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