Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid
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 aci...
Published in: | ChemSusChem |
---|---|
Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
2020
|
Subjects: | |
Online Access: | https://eprints.whiterose.ac.uk/164306/ https://eprints.whiterose.ac.uk/164306/1/cssc.202000842.pdf https://doi.org/10.1002/cssc.202000842 |
id |
ftleedsuniv:oai:eprints.whiterose.ac.uk:164306 |
---|---|
record_format |
openpolar |
spelling |
ftleedsuniv:oai:eprints.whiterose.ac.uk:164306 2023-05-15T13:45:14+02:00 Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid Lie, Yann Pellis, Alessandro Funes-Ardoiz, Ignacio Sampedro, Diego Macquarrie, Duncan J. Farmer, Thomas J. 2020-08-24 text https://eprints.whiterose.ac.uk/164306/ https://eprints.whiterose.ac.uk/164306/1/cssc.202000842.pdf https://doi.org/10.1002/cssc.202000842 en eng https://eprints.whiterose.ac.uk/164306/1/cssc.202000842.pdf 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 cc_by CC-BY Article PeerReviewed 2020 ftleedsuniv https://doi.org/10.1002/cssc.202000842 2023-01-30T22:31:57Z 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. Article in Journal/Newspaper Antarc* Antarctica White Rose Research Online (Universities of Leeds, Sheffield & York) ChemSusChem 13 16 4140 4150 |
institution |
Open Polar |
collection |
White Rose Research Online (Universities of Leeds, Sheffield & York) |
op_collection_id |
ftleedsuniv |
language |
English |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Lie, Yann Pellis, Alessandro Funes-Ardoiz, Ignacio Sampedro, Diego Macquarrie, Duncan J. Farmer, Thomas J. |
spellingShingle |
Lie, Yann Pellis, Alessandro Funes-Ardoiz, Ignacio Sampedro, Diego Macquarrie, Duncan J. Farmer, Thomas J. Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid |
author_facet |
Lie, Yann Pellis, Alessandro Funes-Ardoiz, Ignacio Sampedro, Diego Macquarrie, Duncan J. Farmer, Thomas J. |
author_sort |
Lie, Yann |
title |
Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid |
title_short |
Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid |
title_full |
Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid |
title_fullStr |
Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid |
title_full_unstemmed |
Work-hardening Photopolymer from Renewable Photoactive 3,3’-(2,5-Furandiyl)bisacrylic Acid |
title_sort |
work-hardening photopolymer from renewable photoactive 3,3’-(2,5-furandiyl)bisacrylic acid |
publishDate |
2020 |
url |
https://eprints.whiterose.ac.uk/164306/ https://eprints.whiterose.ac.uk/164306/1/cssc.202000842.pdf https://doi.org/10.1002/cssc.202000842 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://eprints.whiterose.ac.uk/164306/1/cssc.202000842.pdf 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 |
op_rights |
cc_by |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/10.1002/cssc.202000842 |
container_title |
ChemSusChem |
container_volume |
13 |
container_issue |
16 |
container_start_page |
4140 |
op_container_end_page |
4150 |
_version_ |
1766217664031621120 |