Lie, Yann, Pellis, Alessandro, Funes-Ardoiz, Ignacio et al. (3 more authors) (2020) Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid. ChemSusChem. pp. 4140-4150. ISSN 1864-564X
Abstract
The design of a photopolymer around a renewable furan-derived chromophore is presented herein. An optimised semi-continuous oxidation method using MnO2 affords 2,5-diformylfuran from 5-(hydroxymethyl)furfural in gram quantities, allowing the subsequent synthesis of 3,3’-(2,5-furandiyl)bisacrylic acid in good yield and excellent stereoselectivity. The photoactivity of the diester of this monomer is confirmed by reaction under UV irradiation, and the proposed [2+2] cycloaddition mechanism supported further by TD-DFT calculations. Oligoesters of the photoreactive furan diacid with various aliphatic diols are prepared via chemo- and enzyme-catalysed polycondensation. The latter enzyme-catalysed (Candida antarctica lipase B) method results in the highest Mn (3.6 kDa), suggesting milder conditions employed with this protocol minimised unwanted side reactions, including untimely [2+2] cycloadditions, whilst preserving the monomer's photoactivity and stereoisomerism. The photoreactive polyester is solvent cast into a film where subsequent initiator-free UV curing leads to an impressive increase in the material stiffness, with work-hardening characteristics observed during tensile strength testing.
Metadata
Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2020 The Authors. | ||||||
Keywords: | density functional theory, enzyme catalysis, furandiyl diacrylic esters, photochemistry, renewable polyester | ||||||
Dates: |
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Institution: | The University of York | ||||||
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) | ||||||
Funding Information: |
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Depositing User: | Pure (York) | ||||||
Date Deposited: | 11 Aug 2020 15:20 | ||||||
Last Modified: | 31 Jan 2024 01:03 | ||||||
Published Version: | https://doi.org/10.1002/cssc.202000842 | ||||||
Status: | Published | ||||||
Refereed: | Yes | ||||||
Identification Number: | https://doi.org/10.1002/cssc.202000842 | ||||||
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