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...
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Online Access: | http://hdl.handle.net/11567/1062429 https://doi.org/10.1002/cssc.202000842 |
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ftunivgenova:oai:iris.unige.it:11567/1062429 2024-04-14T08:01:45+00:00 Work‐hardening Photopolymer from Renewable Photoactive 3,3’‐(2,5‐Furandiyl)bisacrylic Acid Yann Lie Pellis A Funes‐Ardoiz I Sampedro D Duncan J. Macquarrie Thomas J. Farmer Yann, Lie Pellis, A Funes‐ardoiz, I Sampedro, D Duncan J., Macquarrie Thomas J., Farmer 2020 ELETTRONICO http://hdl.handle.net/11567/1062429 https://doi.org/10.1002/cssc.202000842 eng eng Wiley info:eu-repo/semantics/altIdentifier/wos/WOS:000553221000001 volume:13 (16) firstpage:4140 lastpage:4150 numberofpages:11 journal:CHEMSUSCHEM http://hdl.handle.net/11567/1062429 doi:10.1002/cssc.202000842 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85088803438 info:eu-repo/semantics/openAccess info:eu-repo/semantics/article 2020 ftunivgenova https://doi.org/10.1002/cssc.202000842 2024-03-21T02:37:55Z 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 Università degli Studi di Genova: CINECA IRIS ChemSusChem 13 16 4140 4150 |
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Università degli Studi di Genova: CINECA IRIS |
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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. |
author2 |
Yann, Lie Pellis, A Funes‐ardoiz, I Sampedro, D Duncan J., Macquarrie Thomas J., Farmer |
format |
Article in Journal/Newspaper |
author |
Yann Lie Pellis A Funes‐Ardoiz I Sampedro D Duncan J. Macquarrie Thomas J. Farmer |
spellingShingle |
Yann Lie Pellis A Funes‐Ardoiz I Sampedro D Duncan J. Macquarrie Thomas J. Farmer Work‐hardening Photopolymer from Renewable Photoactive 3,3’‐(2,5‐Furandiyl)bisacrylic Acid |
author_facet |
Yann Lie Pellis A Funes‐Ardoiz I Sampedro D Duncan J. Macquarrie Thomas J. Farmer |
author_sort |
Yann Lie |
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 |
publisher |
Wiley |
publishDate |
2020 |
url |
http://hdl.handle.net/11567/1062429 https://doi.org/10.1002/cssc.202000842 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:000553221000001 volume:13 (16) firstpage:4140 lastpage:4150 numberofpages:11 journal:CHEMSUSCHEM http://hdl.handle.net/11567/1062429 doi:10.1002/cssc.202000842 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85088803438 |
op_rights |
info:eu-repo/semantics/openAccess |
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 |
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1796310600004927488 |