{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T12:13:00Z","timestamp":1788437580139,"version":"build-2803163510"},"reference-count":45,"publisher":"American Chemical Society (ACS)","issue":"34","license":[{"start":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T00:00:00Z","timestamp":1787184000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/na","name":"Carnot Institute ??nergies du futur?","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The equilibrium conversion of 16 model furan derivatives in Diels\u2013Alder (DA) reactions with an aromatic bis-maleimide was investigated across the temperature range of 30\u2013110 \u00b0C. The impact of furan substituents on the reactivity and reversibility of DA adducts was systematically investigated for establishing a useful toolbox of structure\u2013thermal property relationships and clear guidelines for designing reversible furan-maleimide DA-based polymers. Two strategies were considered for furan integration in a polymer network. Monosubstituted furans mimicking grafted-onto moieties were first categorized into two groups: electron-donating substituents (e.g., methylene oxide\/sulfide) achieved \u224890% conversion at 30\u201360 \u00b0C and electron-withdrawing groups (e.g., carboxyl) showed lower conversions (30\u201340%) at 30 \u00b0C but full reversibility at 100 \u00b0C. The heteroatom nature (N, O, or S) poorly affected equilibrium conversion. On the other hand, bisubstituted furans considered for furan integration in the polymer backbone through copolymerization exhibited distinct behaviors: furan-2,5-diyldimethanol (2,5-BHMF) mirrored monofunctional trends, while dimethyl 3,4-furandicarboxylate (3,4-DMFC) interestingly peaked at 76% conversion at 70 \u00b0C. For each studied pair, the endo\/exo adduct ratios continuously evolved toward the more stable exo adduct, potentially modifying network reversibility over time. This library of equilibrium conversions with temperature covers the main commercially available furans and can be used as a selection guide when designing a reversible cross-linked system.<\/jats:p>","DOI":"10.1021\/acsomega.6c04887","type":"journal-article","created":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T08:01:23Z","timestamp":1787212883000},"page":"51541-51552","source":"Crossref","is-referenced-by-count":0,"title":["Tools for the Design\nof Diels\u2013Alder-Based Reversible\nPolymer Systems: Reactivity and Reversibility of Furan\/Maleimide Adducts"],"prefix":"10.1021","volume":"11","author":[{"given":"Justine","family":"Solier","sequence":"first","affiliation":[{"name":"Univ. Grenoble Alpes, CEA, Liten, DTNM , ,","place":["Grenoble, France, 38000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1801-5027","authenticated-orcid":true,"given":"Pierre","family":"Piluso","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CEA, Liten, DTNM , ,","place":["Grenoble, France, 38000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthieu","family":"Landa","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CEA, Liten, DEHT , ,","place":["Grenoble, France, 38000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2440-0423","authenticated-orcid":true,"given":"Se\u0301bastien","family":"Rolere","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CEA, Liten, DTNM , ,","place":["Grenoble, France, 38000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,20]]},"reference":[{"issue":"20","key":"2026090307171115600_cit1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201906876","article-title":"Toward Stimuli-Responsive\nDynamic Thermosets through Continuous Development and Improvements\nin Covalent Adaptable Networks (CANs)","volume":"32","author":"Podgo\u0301rski","year":"2020","journal-title":"Adv.\nMater."},{"issue":"12","key":"2026090307171115600_cit2","doi-asserted-by":"publisher","first-page":"7829","DOI":"10.1021\/acs.chemrev.3c00926","article-title":"New Advances in Covalent Network Polymers via Dynamic Covalent Chemistry","volume":"124","author":"Lei","year":"2024","journal-title":"Chem. Rev."},{"issue":"9","key":"2026090307171115600_cit3","doi-asserted-by":"publisher","first-page":"3652","DOI":"10.1021\/cr020452p","article-title":"Dynamic Combinatorial\nChemistry","volume":"106","author":"Corbett","year":"2006","journal-title":"Chem. Rev."},{"issue":"11","key":"2026090307171115600_cit4","doi-asserted-by":"publisher","DOI":"10.1002\/mame.202300133","article-title":"Diels-Alder Macromolecular Networks\nin Recyclable, Repairable and Reprocessable Polymer Composites for\nthe Circular Economy \u2013 A Review","volume":"308","author":"Griffini","year":"2023","journal-title":"Macromol.\nMater. Eng."},{"issue":"1","key":"2026090307171115600_cit5","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.progpolymsci.2012.04.002","article-title":"The Furan\/Maleimide\nDiels\u2013Alder Reaction: A Versatile Click\u2013Unclick Tool\nin Macromolecular Synthesis","volume":"38","author":"Gandini","year":"2013","journal-title":"Prog. Polym. Sci."},{"issue":"10","key":"2026090307171115600_cit6","doi-asserted-by":"publisher","first-page":"779","DOI":"10.1002\/anie.198007791","article-title":"Mechanistic Aspects of Diels-Alder Reactions: A Critical\nSurvey","volume":"19","author":"Sauer","year":"1980","journal-title":"Angew. Chem., Int. Ed. Engl."},{"issue":"19","key":"2026090307171115600_cit7","doi-asserted-by":"publisher","first-page":"7994","DOI":"10.1021\/jo201606z","article-title":"Substituent Effects on the Reversibility of Furan\u2013Maleimide\nCycloadditions","volume":"76","author":"Boutelle","year":"2011","journal-title":"J. Org. Chem."},{"issue":"6","key":"2026090307171115600_cit8","doi-asserted-by":"publisher","DOI":"10.1002\/mame.202100902","article-title":"Furan Polymers:\nState of the Art and Perspectives","volume":"307","author":"Gandini","year":"2022","journal-title":"Macromol.\nMater. Eng."},{"issue":"2","key":"2026090307171115600_cit9","doi-asserted-by":"publisher","first-page":"157","DOI":"10.1002\/macp.201100405","article-title":"Properties\nof Reversible Diels\u2013Alder Furan\/Maleimide Polymer Networks\nas Function of Crosslink Density","volume":"213","author":"Toncelli","year":"2012","journal-title":"Macromol.\nChem. Phys."},{"key":"2026090307171115600_cit10","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1002\/9781119888710.ch6","article-title":"The Furan\/Maleimide\nDiels\u2013Alder Reaction Applied to Polymer Synthesis and Modification","volume-title":"Furan Polymers and their Reactions","author":"Gandini","year":"2023"},{"issue":"13","key":"2026090307171115600_cit11","doi-asserted-by":"publisher","DOI":"10.1002\/marc.202200023","article-title":"Designing End-of-Life\nRecyclable Polymers via Diels\u2013Alder Chemistry: A Review on\nthe Kinetics of Reversible Reactions","volume":"43","author":"Van Den Tempel","year":"2022","journal-title":"Macromol.\nRapid Commun."},{"issue":"13","key":"2026090307171115600_cit12","doi-asserted-by":"publisher","first-page":"4273","DOI":"10.1039\/D0CS00041H","article-title":"Recent Catalytic Routes for the Preparation\nand the Upgrading of Biomass Derived Furfural and 5-Hydroxymethylfurfural","volume":"49","author":"Xu","year":"2020","journal-title":"Chem. 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Chem. Int. Ed"},{"issue":"1","key":"2026090307171115600_cit18","doi-asserted-by":"publisher","first-page":"30","DOI":"10.3390\/pr10010030","article-title":"Diels\u2013Alder Cycloadditions\nof Bio-Derived Furans with Maleimides as a Sustainable \u226aClick\u226b\nApproach towards Molecular, Macromolecular and Hybrid Systems","volume":"10","author":"Galkin","year":"2022","journal-title":"Processes"},{"issue":"48","key":"2026090307171115600_cit19","doi-asserted-by":"publisher","first-page":"10431","DOI":"10.1021\/acs.jpca.4c05470","article-title":"Computational Insights into Tunable Reversible Network\nMaterials: Accelerated ReaxFF Kinetics of Furan-Maleimide Diels\u2013Alder\nReactions for Self-Healing and Recyclability","volume":"128","author":"Vermeersch","year":"2024","journal-title":"J. Phys. Chem. A"},{"issue":"13","key":"2026090307171115600_cit20","doi-asserted-by":"publisher","first-page":"6024","DOI":"10.1021\/acs.macromol.4c00832","article-title":"Exploring\nPolymeric Diene\u2013Dienophile\nPairs for Thermoreversible Diels\u2013Alder Reactions","volume":"57","author":"MacKinnon","year":"2024","journal-title":"Macromolecules"},{"issue":"4","key":"2026090307171115600_cit21","doi-asserted-by":"publisher","first-page":"473","DOI":"10.1039\/C8PY01216D","article-title":"The Influence of Stereochemistry\non the Reactivity of the Diels\u2013Alder Cycloaddition and the\nImplications for Reversible Network Polymerization","volume":"10","author":"Cuvellier","year":"2019","journal-title":"Polym. Chem."},{"issue":"1","key":"2026090307171115600_cit22","doi-asserted-by":"publisher","first-page":"412","DOI":"10.1021\/acs.macromol.0c02491","article-title":"Time-Temperature-Transformation, Temperature-Conversion-Transformation,\nand Continuous-Heating-Transformation Diagrams of Reversible Covalent\nPolymer Networks","volume":"54","author":"Mangialetto","year":"2021","journal-title":"Macromolecules"},{"key":"2026090307171115600_cit23","volume-title":"Principles of Polymer\nChemistry","author":"Flory","year":"1953"},{"issue":"8","key":"2026090307171115600_cit24","doi-asserted-by":"publisher","first-page":"2230","DOI":"10.3390\/molecules26082230","article-title":"Maleimide Self-Reaction in Furan\/Maleimide-Based\nReversibly Crosslinked\nPolyketones: Processing Limitation or Potential Advantage?","volume":"26","author":"Orozco","year":"2021","journal-title":"Molecules"},{"key":"2026090307171115600_cit25","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.4c03804","article-title":"Diels\u2013Alder\nCycloaddition\nof 2,5-Bis(Hydroxymethyl)Furan (BHMF) and N -Phenylmaleimide\nDerivatives","author":"Shukla","year":"2024","journal-title":"ACS Omega"},{"issue":"15","key":"2026090307171115600_cit26","doi-asserted-by":"publisher","first-page":"3456","DOI":"10.1002\/pola.24134","article-title":"Stereoisomeric\nEffects in Thermo-remendable Polymer Networks Based on Diels\u2013Alder\nCrosslink Reactions","volume":"48","author":"Canadell","year":"2010","journal-title":"J. Polym. Sci. A Polym.\nChem."},{"key":"2026090307171115600_cit27","unstructured":"RadTech.\n          . RadTech. https:\/\/www.radtech.org\/proceedings\/2004\/papers\/084.pdf (accessed\n2025\u201311\u201328)."},{"issue":"5560","key":"2026090307171115600_cit28","doi-asserted-by":"publisher","first-page":"1698","DOI":"10.1126\/science.1065879","article-title":"A Thermally\nRe-Mendable\nCross-Linked Polymeric Material","volume":"295","author":"Chen","year":"2002","journal-title":"Science"},{"issue":"9","key":"2026090307171115600_cit29","doi-asserted-by":"publisher","first-page":"1011","DOI":"10.1007\/s10118-018-2107-x","article-title":"Synthesis\nand Characterization of Butyl Acrylate-Based Graft Polymers\nwith Thermo-Responsive Branching Sites via the Diels-Alder Reaction\nof Furan\/Maleimide","volume":"36","author":"Ye","year":"2018","journal-title":"Chin J. Polym. Sci."},{"issue":"15","key":"2026090307171115600_cit30","doi-asserted-by":"publisher","first-page":"5503","DOI":"10.1039\/D1GC01535D","article-title":"Furoic Acid and Derivatives as Atypical Dienes in Diels\u2013Alder\nReactions","volume":"23","author":"Cioc","year":"2021","journal-title":"Green Chem."},{"issue":"11","key":"2026090307171115600_cit31","doi-asserted-by":"publisher","first-page":"4220","DOI":"10.1021\/jo070373j","article-title":"Toward\nan Understanding of the Acceleration of Diels\u2013Alder Reactions\nby a Pseudo-Intramolecular Process Achieved by Molecular Recognition.\nA DFT Study","volume":"72","author":"Domingo","year":"2007","journal-title":"J. Org. Chem."},{"issue":"12","key":"2026090307171115600_cit32","doi-asserted-by":"publisher","first-page":"3629","DOI":"10.1021\/jf026198j","article-title":"Generation\nof Thiols by Biotransformation of Cysteine\u2013Aldehyde Conjugates\nwith Baker\u2019s Yeast","volume":"51","author":"Huynh-Ba","year":"2003","journal-title":"J. Agric. Food Chem."},{"issue":"7","key":"2026090307171115600_cit33","doi-asserted-by":"publisher","first-page":"461","DOI":"10.22034\/ecc.2021.279489.1158","article-title":"Synthesis of New Heterocyclic\nDerivatives from 2-Furyl\nMethanethiol and Study Their Applications","volume":"3","author":"Maged","year":"2021","journal-title":"Eurasian\nChem. Commun."},{"issue":"6","key":"2026090307171115600_cit34","doi-asserted-by":"publisher","first-page":"5963","DOI":"10.1021\/acssuschemeng.8b06054","article-title":"Microwave-Assisted\nReductive Amination\nwith Aqueous Ammonia: Sustainable Pathway Using Recyclable Magnetic\nNickel-Based Nanocatalyst","volume":"7","author":"Manzoli","year":"2019","journal-title":"ACS Sustainable Chem.\nEng."},{"issue":"11","key":"2026090307171115600_cit35","doi-asserted-by":"publisher","first-page":"2649","DOI":"10.1002\/cctc.201900304","article-title":"A Comprehensive Study\non the Reductive Amination of\n5-Hydroxymethylfurfural into 2,5-Bisaminomethylfuran over Raney Ni\nThrough DFT Calculations","volume":"11","author":"Zhou","year":"2019","journal-title":"ChemCatChem"},{"issue":"2","key":"2026090307171115600_cit36","doi-asserted-by":"publisher","first-page":"157","DOI":"10.1002\/macp.201100405","article-title":"Properties\nof Reversible Diels\u2013Alder Furan\/Maleimide Polymer Networks\nas Function of Crosslink Density","volume":"213","author":"Toncelli","year":"2012","journal-title":"Macromol.\nChem. Phys."},{"issue":"15","key":"2026090307171115600_cit37","doi-asserted-by":"publisher","first-page":"2522","DOI":"10.3390\/polym13152522","article-title":"The Influence of the Furan and Maleimide Stoichiometry\non the Thermoreversible Diels\u2013Alder Network Polymerization","volume":"13","author":"Safaei","year":"2021","journal-title":"Polymers"},{"issue":"23","key":"2026090307171115600_cit38","doi-asserted-by":"publisher","first-page":"9479","DOI":"10.1039\/D1GC02865K","article-title":"Design of Closed-Loop\nRecycling Production of a Diels\u2013Alder Polymer from a Biomass-Derived\nDifuran as a Functional Additive for Polyurethanes","volume":"23","author":"Chang","year":"2021","journal-title":"Green Chem."},{"issue":"12","key":"2026090307171115600_cit39","doi-asserted-by":"publisher","first-page":"4355","DOI":"10.1039\/D1GC00899D","article-title":"Synthesis of Performance-Advantaged\nPolyurethanes and Polyesters from Biomass-Derived Monomers by Aldol-Condensation\nof 5-Hydroxymethyl Furfural and Hydrogenation","volume":"23","author":"Chang","year":"2021","journal-title":"Green Chem."},{"issue":"2","key":"2026090307171115600_cit40","doi-asserted-by":"publisher","first-page":"216","DOI":"10.1002\/pola.26990","article-title":"Biobased Poly(2,5-furandimethylene\nSuccinate- Co -butylene Succinate) Crosslinked by\nReversible Diels\u2013Alder Reaction","volume":"52","author":"Ikezaki","year":"2014","journal-title":"J. Polym.\nSci., Part A: Polym. Chem."},{"key":"2026090307171115600_cit41","doi-asserted-by":"publisher","first-page":"13","DOI":"10.1016\/j.polymdegradstab.2019.01.007","article-title":"Self-Healing\nof Biobased Furan Polymers:\nRecovery of High Mechanical Strength by Mild Heating","volume":"161","author":"Yoshie","year":"2019","journal-title":"Polym. Degrad. Stab."},{"issue":"36","key":"2026090307171115600_cit42","doi-asserted-by":"publisher","first-page":"15678","DOI":"10.1039\/C3RA42457J","article-title":"Concurrent\nFormation of Furan-2,5- and Furan-2,4-Dicarboxylic Acid: Unexpected\nAspects of the Henkel Reaction","volume":"3","author":"Thiyagarajan","year":"2013","journal-title":"RSC Adv."},{"issue":"10","key":"2026090307171115600_cit43","doi-asserted-by":"publisher","first-page":"8991","DOI":"10.1021\/acsomega.2c07629","article-title":"Biobased 2,5-Bis(Hydroxymethyl)Furan\nas a Versatile Building Block\nfor Sustainable Polymeric Materials","volume":"8","author":"Post","year":"2023","journal-title":"ACS Omega"},{"issue":"5","key":"2026090307171115600_cit44","doi-asserted-by":"publisher","first-page":"1794","DOI":"10.1021\/ma3023603","article-title":"Bio-Based\nFuran Polymers with Self-Healing Ability","volume":"46","author":"Zeng","year":"2013","journal-title":"Macromolecules"},{"key":"2026090307171115600_cit45","doi-asserted-by":"publisher","DOI":"10.1016\/j.polymer.2023.125884","article-title":"Beyond Diels-Alder: Domino Reactions\nin Furan-Maleimide Click Networks","volume":"274","author":"Van Den Tempel","year":"2023","journal-title":"Polymer"}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c04887","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/34\/51541\/66889221\/acsomega.6c04887.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/34\/51541\/66889221\/acsomega.6c04887.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T11:17:19Z","timestamp":1788434239000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/34\/51541\/5277349\/Tools-for-the-Design-of-Diels-Alder-Based"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,20]]},"references-count":45,"journal-issue":{"issue":"34","published-online":{"date-parts":[[2026,8,20]]},"published-print":{"date-parts":[[2026,9,1]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c04887","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,20]]}}}